Substituted 1,2,5-oxadiazole compounds and their use as herbicides II

ABSTRACT

The present invention relates to substituted 1,2,5-oxadiazole compounds of the formula (I) and the N-oxides and salts thereof and to compositions comprising the same. The invention also relates to the use of the 1,2,5-oxadiazole compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.

This application is a National Stage application of InternationalApplication No. PCT/EP2012/072692, filed Nov. 15, 2012, which claims thebenefit of U.S. Provisional Application No. 61/560,333, filed Nov. 16,2011, the entire contents of which are hereby incorporated herein byreference.

The present invention relates to substituted 1,2,5-oxadiazole compoundsand the N-oxides and salts thereof and to compositions comprising thesame. The invention also relates to the use of the 1,2,5-oxadiazolecompounds or of the compositions comprising such compounds forcontrolling unwanted vegetation. Furthermore, the invention relates tomethods of applying such compounds.

For the purposes of controlling unwanted vegetation, especially incrops, there is an ongoing need for new herbicides which have highactivities and selectivities together with a substantial lack oftoxicity for humans and animals.

EP 0 173 657 A1 describes N-(1,2,5-oxadiazol-3-yl) carboxamides,herbicidal compositions comprising them and the use of such compositionsfor controlling the growth of weeds.

WO 2011/035874 describes N-(1,2,5-oxadiazol-3-yl)benzamides carrying 3substituents in the 2-, 3- and 4-positions of the phenyl ring and theiruse as herbicides.

The N-(1,2,5-oxadiazol-3-yl) carboxamides of the prior art often sufferform insufficient herbicidal activity in particular at low applicationrates and/or unsatisfactory selectivity resulting in a low compatibilitywith crop plants.

Accordingly, it is an object of the present invention to provide further1,2,5-oxadiazole compounds having a strong herbicidal activity, inparticular even at low application rates, a sufficiently low toxicityfor humans and animals and/or a high compatibility with crop plants. The1,2,5-oxadiazole compounds should also show a broad activity spectrumagainst a large number of different unwanted plants.

These and further objectives are achieved by the compounds of formula Idefined below and their N-oxides and also their agriculturally suitablesalts.

It has been found that the above objectives can be achieved bysubstituted 1,2,5-oxadiazole compounds of the general formula I, asdefined below, including their N-oxides and their salts, in particulartheir agriculturally suitable salts.

Therefore, in a first aspect the present invention relates to compoundsof formula I,

wherein

R is selected from the group consisting of hydrogen, cyano, nitro,halogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, O—R^(a),Z—S(O)_(n)—R^(b), Z—C(═O)—R^(c), Z—C(═O)—OR^(d), Z—C(═O)—NR^(e)R^(f),Z—NR^(g)R^(h), Z-phenyl and Z-heterocyclyl, where heterocyclyl is a 5-or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or4 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where phenyl and heterocyclyl areunsubstituted or substituted by 1, 2, 3 or 4 groups R′, which areidentical or different;

CYC indicates a bi- or tricyclic radical of the following formulae Cyc-1or Cyc-2

where

# indicates the point of attachment of the bicyclic radical to thecarbonyl group,

Q, Q′ independently of each other indicate a fused 5-, 6-, 7-, 8-, 9- or10-membered carbocycle or a fused 5-, 6-, 7-, 8-, 9- or 10-memberedheterocycle, where the fused heterocycle has 1, 2, 3 or 4 heteroatomsselected from O, S and N as ring members, where the fused carbocycle andthe fused heterocycle are monocyclic or bicyclic and where the fusedcarbocycle and the fused heterocycle are unsubstituted or carry 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 radicals R²;

R¹ in formula Cyc-1 is selected from the group consisting of Z¹-cyano,halogen, nitro, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,C₁-C₈-haloalkyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,Z¹—C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylthio-C₁-C₄-alkyl,Z¹—C₁-C₄-alkylthio-C₁-C₄-alkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,Z¹—C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, Z¹—S(O)_(k)—R^(1b), Z¹-phenoxy andZ¹-heterocyclyloxy, where heterocyclyloxy is an oxygen bound 5- or6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or4 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where the cyclic groups in phenoxy andheterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groupsR¹¹, which are identical or different;

R² is selected from the group consisting of halogen, Z²—OH, Z²—NO₂,Z²-cyano, oxo (═O), ═N—R²², C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, Z²—C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, Z²—C₁-C₄-haloalkoxy,Z²—C₃-C₁₀-cycloalkyl, O—Z²—C₃-C₁₀-cycloalkyl, Z²-(tri-C₁-C₄-alkyl)silyl,Z²—S(O)_(k)—R^(2b), Z²—C(═O)—R^(2c), Z²—NR^(2g)R^(2h) and Z²-phenyl,where phenyl in Z²-phenyl is unsubstituted or substituted by 1, 2, 3 or4 groups R²¹, which are identical or different;

R³ in formula Cyc-2 is selected from the group consisting of hydrogen,halogen, Z³—OH, Z³—NO₂, Z³-cyano, C₁-C₆-alkyl, C₂-C₈-alkenyl,C₂-C₈-alkynyl, Z³—C₃-C₁₀-cycloalkyl, Z³—C₃-C₁₀-cycloalkoxy, where theC₃-C₁₀-cycloalkyl groups in the two aforementioned radicals areunsubstituted or partially or completely halogenated, C₁-C₈-haloalkyl,Z³—C₁-C₈-alkoxy, Z³—C₁-C₈-haloalkoxy, Z³—C₁-C₄-alkoxy-C₁-C₄-alkoxy,Z³—C₁-C₄-alkylthio-C₁-C₄-alkylthio, Z³—C₂-C₈-alkenyloxy,Z³—C₂-C₈-alkynyloxy, Z³—C₁-C₈-haloalkoxy,Z³—C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, Z³-(tri-C₁-C₄-alkyl)silyl,Z³—S(O)_(k)—R^(3b), Z³—C(═O)—R^(3c), Z³—C(═O)—OR^(3d),Z³—C(═O)—NR^(3e)R^(3f), Z³—NR^(3g)R^(3h), Z^(3a)-phenyl andZ^(3a)-heterocyclyl, where heterocyclyl is a 3-, 4-, 5- or 6-memberedmonocyclic or 8-, 9- or 10-membered bicyclic saturated, partiallyunsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where the cyclic groups in Z^(3a)-phenyl andZ^(3a)-heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4groups R³¹, which are identical or different;

R⁴ is selected from the group consisting of hydrogen, halogen, cyano,nitro, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

R⁵ is selected from the group consisting of hydrogen, halogen,C₁-C₄-alkyl and C₁-C₄-haloalkyl;

n is 0, 1 or 2;

k is 0, 1 or 2;

R′, R¹¹, R²¹, R³¹ independently of each other are selected from thegroup consisting of halogen, NO₂, CN, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-halocycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₆-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₃-C₇-cycloalkoxy and C₁-C₆-haloalkyloxy;

R²² is selected from the group consisting of C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and C₃-C₇-cycloalkoxy, which is unsubstituted orpartially or completely halogenated;

Z, Z¹, Z², Z³ independently of each other are selected from the groupconsisting of a covalent bond and C₁-C₄-alkanediyl;

Z^(3a) is selected from the group consisting of a covalent bond,C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-O andC₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl;

R^(a) is selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where theC₃-C₇-cycloalkyl groups in the two aforementioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl areunsubstituted or substituted by 1, 2, 3 or 4 groups, which are identicalor different and selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(b), R^(1b), R^(2b), R^(3b) independently of each other are selectedfrom the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl and phenyl, where phenyl is unsubstituted orsubstituted by 1, 2, 3 or 4 groups, which are identical or different andselected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(c), R^(2c), R^(3c) independently of each other are selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aforementioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl,benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-memberedmonocyclic saturated, partially unsaturated or aromatic heterocycle,which contains 1, 2, 3 or 4 heteroatoms as ring members, which areselected from the group consisting of O, N and S, where phenyl, benzyland heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groupsselected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(d), R^(3d) independently of each other are selected from the groupconsisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aforementioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2, 3 or 4 groups, which are identical or different and selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy;

R^(e), R^(f) independently of each other are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aforementioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2, 3 or 4 groups, which are identical or different and selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy, or

R^(e), R^(f) together with the nitrogen atom, to which they are boundmay form a 5-, 6 or 7-membered, saturated or unsaturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 groups, which are identical or different and selectedfrom the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(3e), R^(3f) independently of each other have the meanings given forR^(e), R^(f);

R^(g) is from the group consisting of hydrogen, C₁-C₆-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where theC₃-C₇-cycloalkyl groups in the two aforementioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl areunsubstituted or substituted by 1, 2, 3 or 4 groups, which are identicalor different and selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(h) is selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where theC₃-C₇-cycloalkyl groups in the two aforementioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, a radical C(═O)—R^(k), phenyl and benzyl,where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4groups, which are identical or different and selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy, or

R^(g), R^(h) together with the nitrogen atom, to which they are boundmay form a 5-, 6 or 7-membered, saturated or unsaturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 groups, which are identical or different and selectedfrom the group consisting of ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(2g), R^(2h) independently of each other have the meanings given forR^(g), R^(h);

R^(3g), R^(3h) independently of each other have the meanings given forR^(g), R^(h);

R^(k) has the meanings given for R^(c);

or an N-oxide or an agriculturally suitable salt thereof.

The compounds of the present invention, i.e. the compounds of formula I,their N-oxides, or their salts are particularly useful for controllingunwanted vegetation. Therefore, the invention also relates to the use ofa compound of the present invention, an N-oxide or a salt thereof forcombating or controlling unwanted vegetation.

The invention also relates to a composition comprising at least onecompound according to the invention, including an N-oxide or a saltthereof, and at least one auxiliary. In particular, the inventionrelates to an agricultural composition comprising at least one compoundaccording to the invention including an N-oxide or an agriculturallysuitable salt thereof, and at least one auxiliary customary for cropprotection formulations.

The present invention also relates to the use of a compositioncomprising at least one compound of the invention, an N-oxide or anagriculturally suitable salt thereof, for combating or controllingunwanted vegetation.

The present invention also relates to a method for combating orcontrolling unwanted vegetation, which method comprises allowing aherbicidally effective amount of at least one compound according to theinvention, including an N-oxide or a salt thereof, to act on unwantedplants, their seed and/or their habitat.

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. The inventionprovides both the pure enantiomers or pure diastereomers of thecompounds of formula I, and their mixtures and the use according to theinvention of the pure enantiomers or pure diastereomers of the compoundof formula I or its mixtures. Suitable compounds of the formula I alsoinclude all possible geometrical stereoisomers (cis/trans isomers) andmixtures thereof. Cis/trans isomers may be present with respect to analkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond oramide group. The term “stereoisomer(s)” encompasses both opticalisomers, such as enantiomers or diastereomers, the latter existing dueto more than one center of chirality in the molecule, as well asgeometrical isomers (cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay be present in the form of their tautomers. Hence the invention alsorelates to the tautomers of the formula I and the stereoisomers, saltsand N-oxides of said tautomers.

The term “N-oxide” includes any compound of the present invention whichhas at least one tertiary nitrogen atom that is oxidized to an N-oxidemoiety. N-oxides in compounds I can in particular be prepared byoxidizing the ring nitrogen atom(s) of the oxadiazole ring with asuitable oxidizing agent, such as peroxo carboxylic acids or otherperoxides, or the ring nitrogen atom(s) of a heterocyclic substituent R,R¹, R² or R³.

The present invention moreover relates to compounds as defined herein,wherein one or more of the atoms depicted in formula I have beenreplaced by its stable, preferably non-radioactive isotope (e.g.,hydrogen by deuterium, ¹²C by ¹³C, ¹⁴N by ¹⁵N, ¹⁶O by ¹⁸O) and inparticular wherein at least one hydrogen atom has been replaced by adeuterium atom. Of course, the compounds according to the inventioncontain more of the respective isotope than this naturally occurs andthus is anyway present in the compounds I.

The compounds of the present invention may be amorphous or may exist inone ore more different crystalline states (polymorphs) which may havedifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of formula I, their enantiomersor diastereomers, mixtures of different crystalline states of therespective compound of formula I, its enantiomers or diastereomers, aswell as amorphous or crystalline salts thereof.

Salts of the compounds of the present invention are preferablyagriculturally suitable salts. They can be formed in a customary method,e.g. by reacting the compound with an acid if the compound of thepresent invention has a basic functionality or by reacting the compoundwith a suitable base if the compound of the present invention has anacidic functionality.

Useful agriculturally suitable salts are especially the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, do not have any adverse effect on the herbicidalaction of the compounds according to the present invention. Suitablecations are in particular the ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium, magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzyl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting compounds of the presentinvention with an acid of the corresponding anion, preferably withhydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid ornitric acid.

The term “undesired vegetation” is understood to include any vegetationgrowing at a crop plant site or locus of seeded and otherwise desiredcrop, where the vegetation is any plant species, including theirgerminant seeds, emerging seedlings and established vegetation, otherthan the seeded or desired crop.

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members. The prefix C_(n)-C_(m) indicates in eachcase the possible number of carbon atoms in the group.

The term “halogen” denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “partially or completely halogenated” will be taken to meanthat 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of agiven radical have been replaced by a halogen atom, in particular byfluorine or chlorine. A partially or completely halogenated radical istermed below also “halo-radical”. For example, partially or completelyhalogenated alkyl is also termed haloalkyl.

The term “alkyl” as used herein (and in the alkyl moieties of othergroups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl,alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes ineach case a straight-chain or branched alkyl group having usually from 1to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples ofC₁-C₄-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl,2-butyl(sec-butyl), isobutyl and tert-butyl. Examples for C₁-C₆-alkylare, apart those mentioned for C₁-C₄-alkyl, n-pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-2-methylpropyl. Examples for C₁-C₁₀-alkyl are, apart thosementioned for C₁-C₆-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl,3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl,2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methyloctyl, 2-methylheptyl,1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl,2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.

The term “alkylene” (or alkanediyl) as used herein in each case denotesan alkyl radical as defined above, wherein one hydrogen atom at anyposition of the carbon backbone is replaced by one further binding site,thus forming a bivalent moiety.

The term “haloalkyl” as used herein (and in the haloalkyl moieties ofother groups comprising a haloalkyl group, e.g. haloalkoxy,haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl andhaloalkylsulfinyl) denotes in each case a straight-chain or branchedalkyl group having usually from 1 to 8 carbon atoms (“C₁-C₈-haloalkyl”),frequently from 1 to 6 carbon atoms (“C₁-C₆-haloalkyl”), more frequently1 to 4 carbon atoms (“C₁-C₄-haloalkyl”), wherein the hydrogen atoms ofthis group are partially or totally replaced with halogen atoms.Preferred haloalkyl moieties are selected from C₁-C₄-haloalkyl, morepreferably from C₁-C₂-haloalkyl, more preferably from halomethyl, inparticular from C₁-C₂-fluoroalkyl. Halomethyl is methyl in which 1, 2 or3 of the hydrogen atoms are replaced by halogen atoms. Examples arebromomethyl, chloromethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples forC₁-C₂-fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,pentafluoroethyl, and the like. Examples for C₁-C₂-haloalkyl are, apartthose mentioned for C₁-C₂-fluoroalkyl, chloromethyl, dichloromethyl,trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 2,2,-dichloroethyl,2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl,and the like. Examples for C₁-C₄-haloalkyl are, apart those mentionedfor C₁-C₂-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl,3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl,1,1,1-trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.

The term “cycloalkyl” as used herein (and in the cycloalkyl moieties ofother groups comprising a cycloalkyl group, e.g. cycloalkoxy andcycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphaticradical having usually from 3 to 10 carbon atoms (“C₃-C₁₀-cycloalkyl”),preferably 3 to 7 carbon atoms (“C₃-C₇-cycloalkyl”) or in particular 3to 6 carbon atoms (“C₃-C₆-cycloalkyl”). Examples of monocyclic radicalshaving 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbonatoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl andcycloheptyl. Examples of bicyclic radicals having 7 or 8 carbon atomscomprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl,bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl andbicyclo[3.2.1]octyl.

The term “halocycloalkyl” as used herein (and in the halocycloalkylmoieties of other groups comprising an halocycloalkyl group, e.g.halocycloalkylmethyl) denotes in each case a mono- or bicycliccycloaliphatic radical having usually from 3 to 10 carbon atoms,preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms,wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms arereplaced by halogen, in particular by fluorine or chlorine. Examples are1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl,1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl,1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-, 2- and3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-,2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, 1,2-, 2,2-,2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.

The term “cycloalkyl-alkyl” used herein denotes a cycloalkyl group, asdefined above, which is bound to the remainder of the molecule via analkylene group. The term “C₃-C₇-cycloalkyl-C₁-C₄-alkyl” refers to aC₃-C₇-cycloalkyl group as defined above which is bound to the remainderof the molecule via a C₁-C₄-alkyl group, as defined above. Examples arecyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl,cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl,cyclohexylpropyl, and the like.

The term “alkenyl” as used herein denotes in each case a monounsaturatedstraight-chain or branched hydrocarbon radical having usually 2 to 8(“C₂-C₈-alkenyl”), preferably 2 to 6 carbon atoms (“C₂-C₆-alkenyl”), inparticular 2 to 4 carbon atoms (“C₂-C₄-alkenyl”), and a double bond inany position, for example C₂-C₄-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₈-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl and the positional isomers thereof.

The term “haloalkenyl” as used herein, which may also be expressed as“alkenyl which may be substituted by halogen”, and the haloalkenylmoieties in haloalkenyloxy and the like refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 8(“C₂-C₈-haloalkenyl”) or 2 to 6 (“C₂-C₆-haloalkenyl”) or 2 to 4(“C₂-C₄-haloalkenyl”) carbon atoms and a double bond in any position,where some or all of the hydrogen atoms in these groups are replaced byhalogen atoms as mentioned above, in particular fluorine, chlorine andbromine, for example chlorovinyl, chloroallyl and the like.

The term “alkynyl” as used herein denotes unsaturated straight-chain orbranched hydrocarbon radicals having usually 2 to 8 (“C₂-C₈-alkynyl”),frequently 2 to 6 (“C₂-C₆-alkynyl”), preferably 2 to 4 carbon atoms(“C₂-C₄-alkynyl”) and one or two triple bonds in any position, forexample C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like,C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and the like.

The term “haloalkynyl” as used herein, which is also expressed as“alkynyl which may be substituted by halogen”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having usually 3 to 8carbon atoms (“C₂-C₈-haloalkynyl”), frequently 2 to 6(“C₂-C₆-haloalkynyl”), preferably 2 to 4 carbon atoms(“C₂-C₄-haloalkynyl”), and one or two triple bonds in any position (asmentioned above), where some or all of the hydrogen atoms in thesegroups are replaced by halogen atoms as mentioned above, in particularfluorine, chlorine and bromine.

The term “alkoxy” as used herein denotes in each case a straight-chainor branched alkyl group usually having from 1 to 8 carbon atoms(“C₁-C₈-alkoxy”), frequently from 1 to 6 carbon atoms (“C₁-C₆-alkoxy”),preferably 1 to 4 carbon atoms (“C₁-C₄-alkoxy”), which is bound to theremainder of the molecule via an oxygen atom. C₁-C₂-Alkoxy is methoxy orethoxy. C₁-C₄-Alkoxy is additionally, for example, n-propoxy,1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.

The term “haloalkoxy” as used herein denotes in each case astraight-chain or branched alkoxy group, as defined above, having from 1to 8 carbon atoms (“C₁-C₈-haloalkoxy”), frequently from 1 to 6 carbonatoms (“C₁-C₆-haloalkoxy”), preferably 1 to 4 carbon atoms(“C₁-C₄-haloalkoxy”), more preferably 1 to 3 carbon atoms(“C₁-C₃-haloalkoxy”), wherein the hydrogen atoms of this group arepartially or totally replaced with halogen atoms, in particular fluorineatoms. C₁-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl,OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F₅.C₁-C₄-Haloalkoxy is additionally, for example, 2-fluoropropoxy,3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy,1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxyor nonafluorobutoxy. C₁-C₆-Haloalkoxy is additionally, for example,5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,6-iodohexoxy or dodecafluorohexoxy.

The term “alkoxyalkyl” as used herein denotes in each case alkyl usuallycomprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein1 carbon atom carries an alkoxy radical usually comprising 1 to 8,frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.“C₁-C₆-Alkoxy-C₁-C₆-alkyl” is a C₁-C₆-alkyl group, as defined above, inwhich one hydrogen atom is replaced by a C₁-C₆-alkoxy group, as definedabove. Examples are CH₂OCH₃, CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃)₂,n-butoxymethyl, (1-methylpropoxy)-methyl, (2-methylpropoxy)methyl,CH₂—OC(CH₃)₃, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl,2-(1-methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)-ethyl,2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)-ethyl,2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl,2-(1-methylethoxy)-propyl, 2-(n-butoxy)-propyl,2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)-propyl,2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl, 3-(ethoxy)-propyl,3-(n-propoxy)-propyl, 3-(1-methylethoxy)-propyl, 3-(n-butoxy)-propyl,3-(1-methylpropoxy)-propyl, 3-(2-methylpropoxy)-propyl,3-(1,1-dimethylethoxy)-propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl,2-(n-propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)-butyl,2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)-butyl,2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl,3-(n-propoxy)-butyl, 3-(1-methylethoxy)-butyl, 3-(n-butoxy)-butyl,3-(1-methylpropoxy)-butyl, 3-(2-methylpropoxy)-butyl,3-(1,1-dimethylethoxy)-butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl,4-(n-propoxy)-butyl, 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl,4-(1-methylpropoxy)-butyl, 4-(2-methylpropoxy)-butyl,4-(1,1-dimethylethoxy)-butyl and the like.

The term “haloalkoxy-alkyl” as used herein denotes in each case alkyl asdefined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical asdefined above, usually comprising 1 to 8, frequently 1 to 6, inparticular 1 to 4, carbon atoms as defined above. Examples arefluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl,1-fluoroethoxymethyl, 2-fluoroethoxymethyl, 1,1-difluoroethoxymethyl,1,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl,1,1,2-trifluoroethoxymethyl, 1,2,2-trifluoroethoxymethyl,2,2,2-trifluoroethoxymethyl, pentafluoroethoxymethyl,1-fluoroethoxy-1-ethyl, 2-fluoroethoxy-1-ethyl,1,1-difluoroethoxy-1-ethyl, 1,2-difluoroethoxy-1-ethyl,2,2-difluoroethoxy-1-ethyl, 1,1,2-trifluoroethoxy-1-ethyl,1,2,2-trifluoroethoxy-1-ethyl, 2,2,2-trifluoroethoxy-1-ethyl,pentafluoroethoxy-1-ethyl, 1-fluoroethoxy-2-ethyl,2-fluoroethoxy-2-ethyl, 1,1-difluoroethoxy-2-ethyl,1,2-difluoroethoxy-2-ethyl, 2,2-difluoroethoxy-2-ethyl,1,1,2-trifluoroethoxy-2-ethyl, 1,2,2-trifluoroethoxy-2-ethyl,2,2,2-trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.

The term “alkylthio” (also alkylsulfanyl or S-alkyl)” as used hereindenotes in each case a straight-chain or branched saturated alkyl groupas defined above, usually comprising 1 to 8 carbon atoms(“C₁-C₈-alkylthio”), frequently comprising 1 to 6 carbon atoms(“C₁-C₆-alkylthio”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkylthio”),which is attached via a sulfur atom at any position in the alkyl group.C₁-C₂-Alkylthio is methyl-thio or ethylthio. C₁-C₄-Alkylthio isadditionally, for example, n-propylthio,1-methylethylthio(isopropylthio), butylthio,1-methylpropylthio(sec-butylthio), 2-methylpropylthio(isobutylthio) or1,1-dimethylethylthio(tert-butylthio). C₁-C₆-Alkylthio is additionally,for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio,1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof.

The term “haloalkylthio” as used herein refers to an alkylthio group asdefined above wherein the hydrogen atoms are partially or completelysubstituted by fluorine, chlorine, bromine and/or iodine.C₁-C₂-Haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂,SCCl₃, chlorofluoromethylthio, dichlorofluoromethylthio,chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio,2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,2,2,2-trichloroethylthio or SC₂F₅. C₁-C₄-Haloalkylthio is additionally,for example, 2-fluoropropylthio, 3-fluoropropylthio,2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio,3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio,3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio,SCH₂—C₂F₅, SCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylthio,1-(CH₂Cl)-2-chloroethylthio, 1-(CH₂Br)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆- Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio.

The terms “alkylsulfinyl” and “S(O)_(n)-alkyl” (wherein n is 1) areequivalent and, as used herein, denote an alkyl group, as defined above,attached via a sulfinyl [S(O)] group. For example, the term“C₁-C₂-alkylsulfinyl” refers to a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl”refers to a C₁-C₄-alkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₆-alkylsulfinyl” refers to a C₁-C₆-alkylgroup, as defined above, attached via a sulfinyl [S(O)] group.C₁-C₂-alkylsulfinyl is methylsulfinyl or ethylsulfinyl.C₁-C₄-alkylsulfinyl is additionally, for example, n-propylsulfinyl,1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl,1-methylpropylsulfinyl(sec-butylsulfinyl),2-methylpropylsulfinyl(isobutyl-sulfinyl) or1,1-dimethylethylsulfinyl(tert-butylsulfinyl). C₁-C₆-alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.

The terms “alkylsulfonyl” and “S(O)_(n)-alkyl” (wherein n is 2) areequivalent and, as used herein, denote an alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₂-alkylsulfonyl”refers to a C₁-C₂-alkyl group, as defined above, attached via a sulfonyl[S(O)₂] group. The term “C₁-C₄-alkylsulfonyl” refers to a C₁-C₄-alkylgroup, as defined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-alkylsulfonyl” refers to a C₁-C₆-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. C₁-C₂-alkylsulfonyl ismethylsulfonyl or ethylsulfonyl. C₁-C₄-alkylsulfonyl is additionally,for example, n-propylsulfonyl, 1-methylethylsulfonyl(isopropylsulfonyl),butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl),2-methylpropylsulfonyl(isobutylsulfonyl) or1,1-dimethylethylsulfonyl(tert-butylsulfonyl). C₁-C₆-alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.

The term “alkylamino” as used herein denotes in each case a group —NHR*,wherein R* is a straight-chain or branched alkyl group usually havingfrom 1 to 6 carbon atoms (“C₁-C₆-alkylamino”), preferably 1 to 4 carbonatoms (“C₁-C₄-alkylamino”). Examples of C₁-C₆-alkylamino aremethylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino,2-butylamino, iso-butylamino, tert-butylamino, and the like.

The term “dialkylamino” as used herein denotes in each case agroup-NR*R^(o), wherein R* and R^(o), independently of each other, are astraight-chain or branched alkyl group each usually having from 1 to 6carbon atoms (“di-(C₁-C₆-alkyl)-amino”), preferably 1 to 4 carbon atoms(“di-(C₁-C₄-alkyl)-amino”). Examples of a di-(C₁-C₆-alkyl)-amino groupare dimethylamino, diethylamino, dipropylamino, dibutylamino,methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino,methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino,ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and thelike.

The suffix “-carbonyl” in a group denotes in each case that the group isbound to the remainder of the molecule via a carbonyl C═O group. This isthe case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl,haloalkoxycarbonyl.

The term “aryl” as used herein refers to a mono-, bi- or tricyclicaromatic hydrocarbon radical such as phenyl or naphthyl, in particularphenyl.

The term “het(ero)aryl” as used herein refers to a mono-, bi- ortricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclicheteroaromatic radical, such as pyridyl, pyrimidyl and the like.

The term “5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclicsaturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4heteroatoms as ring members selected from the groups consisting of N, Oand S” as used herein denotes monocyclic or bicyclic heterocyclicradicals, the monocyclic or bicyclic heterocyclic radicals beingsaturated, unsaturated or aromatic. An unsaturated heterocyclic radicalcontains at least one C—C and/or C—N and/or N—N double bond(s). Apartially unsaturated heterocyclic radical contains less conjugated C—Cand/or C—N and/or N—N double bonds than maximally allowed by the size(s)of the ring(s). A fully unsaturated heterocyclic radical contains asmany conjugated C—C and/or C—N and/or N—N double bonds as allowed by thesize(s) of the ring(s). An aromatic monocyclic heterocyclic radical is afully unsaturated 5- or 6-membered monocyclic heterocyclic radical. Anaromatic bicyclic heterocyclic radical is an 8-, 9- or 10-memberedbicyclic heterocyclic radical consisting of a 5- or 6-memberedheteroaromatic ring which is fused to a phenyl ring or to another 5- or6-membered heteroaromatic ring. The heterocyclic radical may be attachedto the remainder of the molecule via a carbon ring member or via anitrogen ring member. As a matter of course, the heterocyclic ringcontains at least one carbon ring atom. If the ring contains more thanone O ring atom, these are not adjacent.

Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycleinclude: oxirane-2-yl, aziridine-1-yl, aziridine-2-yl, oxetan-2-yl,azetidine-1-yl, azetidine-2-yl, azetidine-3-yl, thietane-1-yl,thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl,pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl,pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl,imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl,oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl,isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl,thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl,isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl,isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl,1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl,1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl,piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl,hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl,hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl,piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yland 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl,morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl,thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl and the like.

Examples of a 5- or 6-membered monocyclic partially unsaturatedheterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- ortetrahydropyrimidinyl, di- or tetrahydro-pyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl and 1,2,4-di- or tetrahydrotriazin-3-yl.

A 5- or 6-membered monocyclic fully unsaturated (including aromatic)heterocyclic ring is e.g. a 5- or 6-membered monocyclic fullyunsaturated (including aromatic) heterocyclic ring. Examples are:2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl,3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl,1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl and 2-pyrazinyl.

Examples of a 5- or 6-membered heteroaromatic ring fused to a phenylring or to a 5- or 6-membered heteroaromatic radical includebenzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl,benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl,chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl,pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.

If two radicals bound on the same nitrogen atom (for example R^(e) andR^(f) or R^(2e) and R^(2f) or R^(g) and R^(h) or R^(2g) and R^(2h))together with the nitrogen atom, to which they are bound, form a 5-, 6or 7-membered, saturated or unsaturated N-bound heterocyclic radical,which may carry as a ring member a further heteroatom selected from O, Sand N, this is for example pyrrolidine-1-yl, pyrazolidin-1-yl,imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl,isothiazolin-2-yl, [1,2,3]-triazolidin-1-yl, [1,2,3]-triazolidin-2-yl,[1,2,4]-triazolidin-1-yl, [1,2,4]-triazolidin-4-yl,[1,2,3]-oxadiazolidin-2-yl, [1,2,3]-oxadiazolidin-3-yl,[1,2,5]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-2-yl,[1,2,4]-oxadiazolidin-4-yl, [1,3,4]-oxadiazolidin-3-yl,[1,2,3]-thiadiazolidin-2-yl, [1,2,3]-thiadiazolidin-3-yl,[1,2,5]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-2-yl,[1,2,4]-thiadiazolidin-4-yl, [1,3,4]-thiadiazolidin-3-yl,piperidin-1-yl, piperazine-1-yl, morpholin-1-yl, thiomorpholin-1-yl,1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl,1,4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl,oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-yl,1,2-dihydropyridin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl,1,2,5,6-tetrahydropyridin-1-yl, 1,2-dihydropyridazin,1,6-dihydropyridazin, 1,2,3,4-tetrahydropyridazin-1-yl,1,2,5,6-tetrahydropyridazin-1-yl, 1,2-dihydropyrimidin,1,6-dihydropyrimidin, 1,2,3,4-tetrahydropyrimidin-1-yl,1,2,5,6-tetrahydropyrimidin-1-yl, 1,2-dihydropyrazin-1-yl,1,2,3,4-tetrahydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl,pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, [1,2,3]-1H-triazol-1-yl,[1,2,3]-2H-triazol-2-yl, [1,2,4]-1H-triazol-1-yl and[1,2,4]-4H-triazol-4-yl.

The term “fused 5-, 6-, 7-, 8-, 9- and 10-membered carbocycle or 5-, 6-,7-, 8-, 9- and 10-membered heterocycle” refers to a carbo- orheterocycle that is adjoined at two consecutive positions with thephenyl group of the radical Cyc-1 or Cyc-1 in such a way that both ringsshare the ring atoms at said two positions. The fused carbo- andheterocycles may be saturated, partially unsaturated or fullyunsaturated and in addition may be mono-, bi- or tricyclic, where eachone of the two or three rings of the bi- and tricyclic fused carbo- andheterocycles is either fused to one or two of the other rings, i.e. tworings share two ring atoms, or spiro-linked, i.e. two rings share 1 ringatom. Examples of 5-, 6-, 7-, 8-, 9- and 10-membered fused carbocyclesare cyclopentane, cyclohexane, cycloheptane, cyclo[3.3.0]octane,cyclo[4.3.0]nonane, cyclo[4.4.0]decane cyclopentene, cyclohexene andbenzene. Examples of 5-, 6-, 7-, 8-, 9- and 10-membered fusedcarbocycles are pyrrolidine, tetrahydrofuran, tetrahydrothiophen,dihydrofuran, dihydrothiophen, pyrrole, furan, thiopene, thiazole,thiazine, piperidine, tetrahydropyran, tetrahydrothiopyrane, dioxane,piperazine, morpholine, pyridine, azepane, oxepane, thiepane, azepine,oxepine, thiepine, pyrazole, pyrazoline, imidazole, benzimidazole,imidazoline, indole, indoline, chinoline, isochinoline, pyrimidine,oxazole, isoxazole, oxazoline, isoxazoline and the like.

The remarks made below as to preferred embodiments of the variables(substituents) of the compounds of formula I are valid on their own aswell as preferably in combination with each other, as well as incombination with the stereoisomers, salts, tautomers or N-oxidesthereof.

The remarks made below concerning preferred embodiments of the variablesfurther are valid on their own as well as preferably in combination witheach other concerning the compounds of formulae I, where applicable, aswell as concerning the uses and methods according to the invention andthe composition according to the invention.

Preferred compounds according to the invention are compounds of formulaI or a stereoisomer, salt or N-oxide thereof, wherein the salt is anagriculturally suitable salt. Further preferred compounds according tothe invention are compounds of formula I or an N-oxide or salt thereof,especially an agriculturally suitable salt. Particularly preferredcompounds according to the invention are compounds of formula I or asalt thereof, especially an agriculturally suitable salt thereof.

According to a preferred embodiment of the invention the variable R inthe compounds of formula I is selected from the group consisting ofhalogen, cyano, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl,C(═O)—R^(c), C(═O)—OR^(d), C(═O)—NR^(e)R^(f), NH—C(═O)R^(k) andNR^(g)R^(h), where R^(c), R^(d), R^(e), R^(f), R^(k), R^(g) and R^(h)are as defined above and which preferably have on their own or inparticular in combination the following meanings:

R^(c) is hydrogen, C₁-C₆-alkyl C₃-C₇-cycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₁-C₆-haloalkyl or phenyl, in particular C₁-C₄-alkylor C₁-C₄-haloalkyl;

R^(d) is C₁-C₆-alkyl or C₁-C₆-haloalkyl, in particular C₁-C₄-alkyl;

R^(e), R^(f) are independently of each other selected from hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl and benzyl, and in particular from thegroup consisting of hydrogen and C₁-C₄-alkyl; or

R^(e), R^(f) together with the nitrogen atom, to which they are boundform a 5-, 6- or 7-membered, saturated or unsaturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 groups, which are identical or different and selectedfrom the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl,and in particular R^(e), R^(f) together with the nitrogen atom, to whichthey are bound may form a 5-, 6- or 7-membered, saturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 methyl groups;

R^(g), R^(h) are independently of each other selected from hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl and benzyl, and in particular from thegroup consisting of hydrogen and C₁-C₄-alkyl, or

R^(g), R^(h) together with the nitrogen atom, to which they are boundform a 5-, 6 or 7-membered, saturated or unsaturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 groups, which are identical or different and selectedfrom the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl,and in particular R^(g), R^(h) together with the nitrogen atom, to whichthey are bound may form a 5-, 6- or 7-membered, saturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 methyl groups; and

R^(k) is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenyl, in particularC₁-C₄-alkyl.

According to a more preferred embodiment the variable R of the compoundsof the formula I is selected from the group consisting of halogen,cyano, nitro, NH₂, C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C(═O)—R^(c), C(═O)—OR^(d),C(═O)—NR^(e)R^(f) and NH—C(═O)R^(k), where R^(c), R^(d), R^(e), R^(f)and R^(k) are as defined above and which preferably have on their own orin particular in combination the following meanings:

R^(c) is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^(d) is C₁-C₄-alkyl,

R^(e) is hydrogen or C₁-C₄-alkyl,

R^(f) is hydrogen or C₁-C₄-alkyl, or

R^(e), R^(f) together with the nitrogen atom, to which they are boundmay form a 5-, 6 or 7-membered, saturated N-bound heterocyclic radical,which may carry as a ring member a further heteroatom selected from O, Sand N and which is unsubstituted or may carry 1, 2, 3 or 4 methylgroups, and

R^(k) is C₁-C₄-alkyl.

According to a particular preferred embodiment of the invention thevariable R in the compounds of formula I is selected from halogen,cyano, nitro, C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl,acetylamino, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl,piperidinylcarbonyl, trifluoromethylcarbonyl, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl and methoxymethyl, inparticular from Cl, Br, F, methyl, ethyl, isopropyl, tert-butyl,cyclopropyl, cyclopentyl, cyclohexyl, CF₃, CHF₂, CClF₂, CH₂CF₃, CF₂CF₃,CH₂Cl, CHCl₂, cyano, nitro, acetylamino, methoxycarbonyl,ethoxycarbonyl, methylcarbonyl, piperidinylcarbonyl,trifluoromethylcarbonyl, amino, aminocarbonyl, methylaminocarbonyl,dimethylaminocarbonyl and methoxymethyl.

According to a further preferred embodiment of the invention thevariable R in the compounds of formula I is a radical OR^(a), whereR^(a) is as defined above and in particular selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which isunsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, preferably from hydrogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which isunsubstituted or partly or completely halogenated, and in particularfrom hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₆-cycloalkyl. In thiscontext R^(a) specifically is hydrogen, CH₃, CH₂H₃, CH(CH₃)₂, CH₂CH₂CH₃,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH₂Cl, C(CH₃)₃, CHF₂,CF₃, CH₂CH═CH₂, CH₂C≡CH, CH₂OCH₃, CH₂CH₂OCH₃ and CH₂CH₂OCH₂CH₃.

According to another preferred embodiment of the invention the variableR in the compounds of formula I is phenyl or heterocyclyl, whereheterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-memberedbicyclic saturated, partially unsaturated or aromatic heterocycle, whichcontains 1, 2, 3 or 4 heteroatoms as ring members, which are selectedfrom the group consisting of O, N and S, where phenyl and heterocyclylare unsubstituted or substituted by 1, 2, 3 or 4 groups R′ which are asdefined above and which are independently from one another preferablyselected from the group consisting of halogen, C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₆-haloalkyloxy, more preferably fromhalogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl andC₁-C₄-alkoxy, in particular from halogen, methyl, ethyl, methoxy andtrifluoromethyl, and specifically from Cl, F, Br, methyl, methoxy andtrifluoromethyl.

According to a more preferred embodiment of the invention the variable Rin the compounds of formula I is phenyl or heterocyclyl, whereheterocyclyl is a partially unsaturated or aromatic 5- or 6-memberedmonocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3or 4 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where the bicyclic heterocycle consists of a5- or 6-membered heteroaromatic ring which is fused to a phenyl ring,and where phenyl and heterocyclyl are unsubstituted or substituted by 1,2, 3 or 4 groups R′ which independently from one another have theaforementioned preferred meanings.

According to particular preferred embodiments the variable R in thecompounds of the formula I is phenyl or heterocyclyl selected frompyridin-2-yl, pyridin-3-yl, pyridin-4-yl, piperidin-2-yl,piperidin-3-yl, piperidin-4-yl, benzisoxazole-2-yl,1,2,4-oxadiazol-3-yl, 1,2,4-triazol-3-yl, 1-ethylbenzimidazol-2-yl,4-methylthiazol-2-yl, thiophen-2-yl, furan-2-yl, furan-3-yl,tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, isoxazol-2-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, oxazol-2-yl, oxazol-3-yl,oxazol-4-yl, oxazol-5-yl, pyrrol-2-yl, pyrrol-3-yl, imidazol-2-yl,imidazol-4-yl, imidazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl,1,2,5-triazol-3-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl,1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,1,2,5-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,1,2,5-thiadiazol-3-yl, 2H-1,2,3,4-tetrazol-5-yl,1H-1,2,3,4-tetrazol-1-yl, 1,2,3,4-oxatriazol-5-yl,1,2,3,5-oxatriazol-4-yl, 1,2,3,4-thiatriazol-5-yl,1,2,3,5-thiatriazol-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl and pyridazin-4-yl, wherephenyl and heterocyclyl are unsubstituted or carry 1, 2, or 3 groups R′which independently from one another have the aforementioned preferredmeanings.

According to a preferred embodiment of the invention the variable R inthe compounds of formula I is S(O)_(n)—R^(b), where R^(b) is as definedabove and in particular selected from the group consisting ofC₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl andheterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclicsaturated, partially unsaturated or aromatic heterocycle, which contains1, 2 or 3 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where phenyl and heterocyclyl areunsubstituted or substituted by 1, 2 or 3 groups, which are identical ordifferent and preferably selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₂-alkoxy.

According to a more preferred embodiment of the invention the variable Rin the compounds of formula I is S(O)_(n)—R^(b), where R^(b) is selectedfrom the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₇-cycloalkyl,phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-memberedmonocyclic saturated, partially unsaturated or aromatic heterocycle,which contains 1, 2 or 3 heteroatoms as ring members, which are selectedfrom the group consisting of O, N and S.

According to an even more preferred embodiment of the invention thevariable R in the compounds of formula I is S(O)_(n)—R^(b), where R^(b)is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, phenyl andheterocyclyl, where heterocyclyl is a 6-membered aromatic heterocyclicradical having 1 or 2 nitrogen atoms as ring members.

According to a particularly preferred embodiment of the invention thevariable R in the compounds of formula I is S(O)₂—R^(b), where R^(b) isCH₃, CH₂H₃, CH(CH₃)₂, CH₂CH₂CH₃, CH₂CH═CH₂, CH₂C≡CH or phenyl.

According to specifically preferred embodiments of the invention thevariable R in the compounds of formula I is selected from the groupconsisting of Cl, Br, F, methyl, ethyl, isopropyl, tert-butyl,cyclopropyl, cyclopentyl, cyclohexyl, CF₃, CHF₂, CClF₂, CH₂CF₃, CF₂CF₃,CH₂Cl, CHF₂, CHCl₂, cyano, nitro, acetylamino, benzoylamino,methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl,piperidinylcarbonyl, trifluoromethylcarbonyl, amino, aminocarbonyl,methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, OH, OCH₃,OCH₂H₃, OCH(CH₃)₂, OCH₂CH₂CH₃, O-cyclopropyl, O-cyclobutyl,O-cyclopentyl, O-cyclohexyl, O—CH₂Cl, O—C(CH₃)₃, O—CHF₂, O—CF₃,O—CH₂CH═CH₂, O—CH₂C≡CH, O—CH₂OCH₃, O—CH₂CH₂OCH₃, O—CH₂CH₂OCH₂CH₃,S(O)₂—CH₃, S(O)₂—CH₂H₃, S(O)₂—CH(CH₃)₂, S(O)₂—CH₂CH₂CH₃,S(O)₂—CH₂CH═CH₂, S(O)₂—CH₂C≡CH and S(O)₂-phenyl, and in particular frommethyl, ethyl and methoxy.

Preferred compounds according to the invention are compounds of formulaI, wherein R², if present, is selected from the group consisting ofhalogen, NO₂, cyano, oxo (═O), ═N—R²², where R²² is as defined above andin particular is C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-haloalkoxy,C₃-C₁₀-cycloalkyl, O—C₃-C₁₀-cycloalkyl, C₁-C₄-alkylsulfonyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)-amino andZ²-phenyl, where Z² is as defined herein, and where phenyl isunsubstituted or carries 1, 2 or 3 radicals R²¹ which are as definedabove and preferably are independently of one another selected fromhalogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy, and morepreferably from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkyl andC₁-C₂-alkoxy-C₁-C₂-alkoxy.

More preferably R², if present, is selected from halogen, NO₂, cyano,oxo, ═N—R²², where R²² is C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-haloalkoxy,C₃-C₁₀-cycloalkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl andbenzyl, where phenyl in the last two mentioned radicals is unsubstitutedor carries 1, 2 or 3 radicals R²¹ which are as defined above and inparticular are independently of one another selected from halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl andC₁-C₄-alkoxy-C₁-C₄-alkoxy.

Even more preferably R², if present, is selected from halogen, oxo,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl, ═N—R²²,where R²² is C₁-C₄-alkoxy, and phenyl, where phenyl is unsubstituted orcarries 1, 2 or 3 radicals R²¹ which are identical or different and areselected from halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy.

Particularly preferred R², if present, is selected from halogen, oxo,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio, C₃-C₄-alkenyl, C₃-C₄-alkynyl and═N—R²², where R²² is C₁-C₄-alkoxy.

In particular, R², if present, is selected from halogen, oxo,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-haloalkoxy,C₃-C₄-alkenyl and ═N—R²², where R²² is C₁-C₄-alkoxy.

Specifically, R², if present, is halogen, oxo, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyl or ═N—R²², where R²² isC₁-C₄-alkoxy, and more specifically F, Cl, ═O, CH₃, CH₂CH₃, CH₂CH₂CH₃,CH(CH₃)₂, CH₂CH═CH₂, OCF₃, OCHF₂, OCH₂F, OCH₂Cl, OCH₂CH₂F, OCF₂CF₃,OCH₃, OCH₂CH₃, ═N—OCH₃ or ═N—OCH₂CH₃.

Preferred compounds according to the invention are compounds of formulaI, wherein R⁴ is selected from the group consisting of hydrogen, cyano,halogen, nitro, C₁-C₂-alkyl and C₁-C₂-haloalkyl, in particular from thegroup consisting of hydrogen, CHF₂, CF₃, CN, NO₂, CH₃ and halogen, whichis preferably from Cl, Br and F. Specifically R⁴ is hydrogen.

Preferred compounds according to the invention are compounds of formulaI, wherein R⁵ is selected from the group consisting of hydrogen,halogen, C₁-C₂-alkyl and C₁-C₂-haloalkyl, and in particular from thegroup consisting of hydrogen, CHF₂, CF₃ and halogen.

According to a particular embodiment of the invention R⁴ and R⁵ are bothhydrogen.

According to a preferred embodiment of the invention the variable CYC inthe compound of formula I is a radical Cyc-1, as defined above.

According to a more preferred embodiment of the invention the variable Qof the radical Cyc-1 indicates a fused 5- or 6-membered monocyclicheterocycle or a fused 7-, 8-, 9- or 10-membered spiro-bicyclicheterocycle, where the fused monocyclic heterocycle has 1 or 2heteroatoms selected from O, S and N as ring members and isunsubstituted or carries 1, 2, 3, 4, 5, 6, 7 or 8 radicals R², where thefused spiro-bicyclic heterocycle has 1, 2, 3 or 4 heteroatoms selectedfrom O, S and N as ring members and is unsubstituted or carries 1, 2, 3,4, 5, 6, 7, 8, 9 or 10 radicals R², where R² has the herein definedmeanings and in particular those mentioned as preferred.

According to an even more preferred embodiment of the invention thevariable Q of the radical Cyc-1 indicates a fused 5- or 6-memberedmonocyclic heterocycle or a fused 8-, 9- or 10-membered spiro-bicyclicheterocycle which are both either saturated or partially unsaturated,where the fused monocyclic heterocycle has 1 or 2 and the fusedspiro-bicyclic heterocycle has 1, 2, 3 or 4 heteroatoms selected from O,S and N as ring members, where S as ring member is unsubstituted or ispart of a S(O)₂ group or a S(O) group, and where one carbon atom that isa ring member of the fused mono-cyclic or spiro-bicyclic heterocycle maybe part of a carbonyl group. In addition, according to this embodimentthe fused monocyclic heterocycle carries 0, 1, 2, 3, 4 or 5 and thefused spiro-bicyclic heterocycle carries 0, 1, 2, 3, 4, 5, 6 or 7radicals R², which have the herein defined meanings and in particularare independently of one another selected from halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₃-C₄-alkenyl and═N—R²², where R²² is C₁-C₄-alkoxy.

According to a particularly preferred embodiment of the invention thevariable Q of the radical Cyc-1 indicates a fused 5- or 6-memberedmonocyclic heterocycle or a fused 8- or 9-membered spiro-bicyclicheterocycle which are both either saturated or partially unsaturated,where the fused monocyclic heterocycle has 1 or 2 and the fusedspiro-bicyclic heterocycle has 1, 2 or 3 heteroatoms selected from O, Sand N as ring members, where S as ring member is unsubstituted or ispart of a S(O)₂ group and where one carbon atom that is a ring member ofthe fused monocyclic or spiro-bicyclic heterocycle may be part of acarbonyl group, where said heterocycle includes one or two S(O)₂ groupsand/or one carbonyl group. In addition, according to this embodiment thefused monocyclic heterocycle carries 0, 1, 2 or 3 and the fusedspiro-bicyclic heterocycle carries 0, 1, 2, 3 or 4 radicals R², whichhave the herein defined meanings and in particular are independently ofone another are selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₃-C₄-alkenyl and ═N—R²², where R²² is C₁-C₄-alkoxy.

According to a particular embodiment of the invention the radical CYC ofthe 1,2,5-oxadiazole compound of the formula I is a radical Cyc-1 thatis selected from the following groups Cyc-1a to Cyc-1h:

where # indicates the point of attachment of the bi- or tricyclicradical to the carbonyl group of the compound of formula I, R¹, R², R⁴and R⁵ have the herein defined meanings, in particular those mentionedas preferred, R⁵ is in particular hydrogen or halogen, especiallyhydrogen, F, Cl or Br, and R²³ and R²⁴ are hydrogen or have one of themeanings given for R² in particular those mentioned as preferred.

According to a specific embodiment of the invention the radical Cyc-1 isselected from the following groups Cyc-1a′ to Cyc-1h′ and Cyc-1f″:

where

# indicates the point of attachment of the bi- or tricyclic radical tothe carbonyl group of the compound of formula I;

R¹ has the herein defined meanings, in particular those mentioned hereinbelow as preferred;

R^(2p), R^(2q) are independently of each other hydrogen, C₁-C₄-alkyl orC₁-C₄-alkoxy, preferably R^(2p) is hydrogen, CH₃, CH₂CH₃ or CH₂(CH₃)₂and R^(2q) is hydrogen, CH₃, CH₂CH₃, CH₂(CH₃)₂, OCH₃ or OCH₂CH₃, and inparticular R^(2p) is hydrogen or CH₃ and R^(2q) is hydrogen, CH₃ orOCH₃;

R^(2r), R^(2s) are independently of each other hydrogen, halogen orC₁-C₄-alkyl, preferably hydrogen or halogen, and in particular hydrogen,fluorine or chlorine;

R^(2t) is C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, preferably C₁-C₄-haloalkoxy,and in particular OCH₂CH₂F;

R^(2u) is C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, preferably C₁-C₄-alkoxy, andin particular OCH₃ or OCH₂CH₃;

R^(2v) is C₁-C₄-alkyl or C₃-C₄-alkenyl, preferably C₁-C₃-alkyl orC₃-C₄-alkenyl, and in particular CH₃, CH₂CH₃, CH₂CH₂CH₃, CH(CH₃)₂ orCH₂CH═CH₂.

According to an even more specific embodiment of the invention theradical Cyc-1 is selected from the following groups Cyc-1a′-1 toCyc-1a′-6, Cyc-1b′, Cyc-1c′, Cyc-1d′-1 to Cyc-1d′-9, Cyc-1e′, Cyc-1f′,Cyc-1f″-1 and Cyc-1f″-2, Cyc-1fg′, and Cyc-1h′-1 to Cyc-1h′-5:

where # indicates the point of attachment of the bi- or tricyclicradical to the carbonyl group of the compound of formula I and R¹ hasthe herein defined meanings, in particular those mentioned herein belowas preferred.

Among the compounds of formula I wherein CYC is Cyc-1, preference isgiven to those compounds, wherein R¹ is selected from the groupconsisting of CN, halogen, nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, Z¹—C₁-C₄-alkoxy-C₁-C₄-alkoxy,C₁-C₄-alkylthio-C₁-C₄-alkyl, Z¹—C₁-C₄-alkylthio-C₁-C₄-alkylthio,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,C₁-C₄-haloalkoxy-C₁-C₄-alkoxy and S(O)_(k)R^(1b), where k and Z¹ are asdefined herein and where R^(1b) is as defined above and in particularselected from the group consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl.In this context Z¹ is in particular a covalent bond.

More preferably, R¹ is selected from halogen, CN, nitro, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkylthio-C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy,C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,S(O)_(k)—C₁-C₄-alkyl and S(O)_(k)—C₁-C₄-haloalkyl, where k is 0 or 2.

In particular, R¹ is selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsufonyl,specifically R¹ is F, Cl, Br, CH₃, CF₃, OCH₃, OCF₃, SCF₃, SO₂CH₃ orCH₂OCH₂CH₂OCH₃, and more specifically R¹ is Cl, CH₃, CF₃ or SO₂CH₃.

According to a preferred embodiment of the invention the variable CYC inthe compound of formula I is a radical Cyc-2, as defined above.

According to a more preferred embodiment of the invention the variableQ′ of the radical Cyc-1 indicates a fused 5- or 6-membered monocyclicheterocycle or a fused 7-, 8-, 9- or 10-membered bicyclic heterocycle,where the fused monocyclic heterocycle has 1 or 2 heteroatoms selectedfrom O, S and N as ring members and is unsubstituted or carries 1, 2, 3,4, 5, 6, 7 or 8 radicals R², where the fused bicyclic heterocycle has 1,2, 3 or 4 heteroatoms selected from O, S and N as ring members and isunsubstituted or carries 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 radicals R²,where R² has the herein defined meanings in particular those mentionedas preferred.

According to an even more preferred embodiment of the invention thevariable Q′ of the radical Cyc-2 indicates a fused 5- or 6-memberedmonocyclic heterocycle or a fused 8-, 9- or 10-membered bicyclicheterocycle which are both either partially unsaturated or fullyunsaturated, where the fused monocyclic heterocycle has 1 or 2 and thefused bicyclic heterocycle has 1, 2, 3 or 4 heteroatoms selected from O,S and N as ring members, and where the fused monocyclic heterocycle isunsubstituted or carries 1, 2, 3, 4, 5 or 6 and the fused bicyclicheterocycle is unsubstituted or carries 1, 2, 3, 4, 5, 6, 7 or 8radicals R², which are as defined herein and in particular areindependently of one another selected from halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₃-C₄-alkenyl and═N—R²², where R²² is C₁-C₄-alkoxy.

According to a particularly preferred embodiment of the invention thevariable Q′ of the radical Cyc-2 indicates a fused aromatic 5- or6-membered monocyclic heterocycle or a fused aromatic 8-, 9- or10-membered bicyclic heterocycle, where the fused monocyclic heterocyclehas 1 or 2 and the fused bicyclic heterocycle has 1, 2 or 3 heteroatomsselected from O and N as ring members, and where the fused monocyclicheterocycle is unsubstituted or carries 1, 2, 3 or 4 and the fusedbicyclic heterocycle is unsubstituted or carries 1, 2, 3, 4, 5 or 6radicals R², which are as defined herein and in particular areindependently of one another selected from halogen, C₁-C₄-alkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkyl.

According to a particular embodiment of the invention the radical CYC ofthe 1,2,5-oxadiazole compound of the formula I is a radical Cyc-2 thatis selected from the following groups Cyc-2a to Cyc-2d:

where # indicates the point of attachment of the bicyclic radical to thecarbonyl group of the compound of formula I, R², R³ and R⁴ have theherein defined meanings, in particular those mentioned as preferred, andp is 0, 1, 2 or 3, preferably is 0 or 1 and in particular is 0.

According to a specific embodiment of the invention the radical Cyc-1 isselected from the following groups Cyc-2a′ to Cyc-2d′:

where # indicates the point of attachment of the bicyclic radical to thecarbonyl group of the compound of formula I and R³ has the hereindefined meanings, in particular those mentioned herein below aspreferred.

Among the compounds of formula I wherein CYC is Cyc-2, preference isgiven to those compounds, wherein R³ is selected from the groupconsisting of hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₂-C₄-alkenyloxy, C₂-C₄-alkynyloxy and S(O)_(k)R^(2b),where the variables k and R^(2b) have one of the herein definedmeanings.

More preferably, R³ is selected from the group consisting of hydrogen,halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,S(O)₂—C₁-C₄-alkyl and S(O)₂—C₁-C₄-haloalkyl.

In particular, R³ is selected from the group consisting of hydrogen,halogen, CN, NO₂, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy,C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio,S(O)₂—C₁-C₂-alkyl and S(O)₂—C₁-C₂-haloalkyl, specifically from hydrogen,Cl, F, CN, NO₂, CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SCF₃, SCHF₂,S(O)₂CH₃ and S(O)₂CH₂CH₃, and more specifically from Cl, F, CN, CF₃ andS(O)₂CH₃.

The variables R′, R¹¹, R²¹, R³¹, Z, Z¹, Z², Z³, Z^(3a), R^(a), R^(b),R^(1b), R^(2b), R^(3b), R^(c), R^(2c), R^(3c), R^(d), R^(3d), R^(e),R^(f), R^(3e), R^(3f), R^(g), R^(h), R^(2g), R^(2h), R^(3g), R^(3h),R^(k), n and k, independently of each other, preferably have one of thefollowing meanings:

R′, R¹¹, R²¹, R³¹ independently of each other are selected from halogen,C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₆-haloalkyloxy, morepreferably from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyland C₁-C₄-alkoxy.

More preferably R′, R¹¹, R²¹, R³¹ independently of each other areselected from the group consisting of halogen, C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-alkoxy-C₁-C₄-alkyl; in particular selected from halogen,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl and C₁-C₄-alkoxy-C₁-C₄-alkyl;and specifically from Cl, F, Br, methyl, ethyl, methoxy andtrifluoromethyl.

R²² is selected from C₁-C₄-alkoxy, C₁-C₄-haloalkoxy andC₃-C₇-cycloalkoxy; more preferably from C₁-C₄-alkoxy andC₁-C₄-haloalkoxy, particularly from C₁-C₄-alkoxy, and specifically isOCH₃ or OCH₂CH₃.

Z, Z¹, Z², Z³ independently of each other are selected from a covalentbond, methanediyl and ethanediyl, and in particular are a covalent bond.

Z^(3a) is selected from a covalent bond, C₁-C₂-alkanediyl,O—C₁-C₂-alkanediyl, C₁-C₂-alkanediyl-O andC₁-C₂-alkanediyl-O—C₁-C₂-alkanediyl; more preferably from a covalentbond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl,methanediyl-O, and ethanediyl-O; and in particular from a covalent bond,methanediyl and ethanediyl.

R^(a) is selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which isunsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl.

More preferably R^(a) is selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted orpartly or completely halogenated, and in particular selected fromhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₆-cycloalkyl.

R^(b), R^(1b), R^(2b), R^(3b) independently of each other are selectedfrom C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl and phenyl, wherephenyl is unsubstituted or substituted by 1, 2 or 3 groups, which areidentical or different and selected from the group consisting ofhalogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₂-alkoxy.

More preferably R^(b), R^(1b), R^(2b), R^(3b) independently of eachother are selected from the group consisting of C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl and phenyl.

In particular, R^(b), R^(1b), R^(2b), R^(3b) independently of each otherare selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl and phenyl.

R^(c), R^(2c), R^(3c), R^(k) independently of each other are selectedfrom hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted orpartly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl and heterocyclyl, whereheterocyclyl is a 5- or 6-membered monocyclic saturated, partiallyunsaturated or aromatic heterocycle, which contains 1, 2 or 3heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where phenyl, benzyl and heterocyclyl areunsubstituted or substituted by 1, 2 or 3 groups, which are identical ordifferent and selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R^(c), R^(2c), R^(3c), R^(k) independently of each otherare selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C-alkenyl,C₂-C-haloalkenyl, C₂-C-alkynyl, C₃-C₆-cycloalkyl, phenyl andheterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclicsaturated, partially unsaturated or aromatic heterocycle, which contains1, 2 or 3 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S.

In particular, R^(c), R^(2c), R^(3c), R^(k) independently of each otherare selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, whereheterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having1 or 2 nitrogen atoms as ring members.

R^(d), R^(3d) independently of each other are selected from C₁-C₆-alkyl,C₃-C₇-cycloalkyl, which is unsubstituted or partly or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl.

More preferably R^(d), R^(3d) independently of each other are selectedfrom C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which isunsubstituted or partly or completely halogenated, and in particularselected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₃-C₆-cycloalkyl.

R^(e), R^(f), R^(3e), R^(3f) independently of each other are selectedfrom the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,which is unsubstituted or partially or completely halogenated,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl areunsubstituted or substituted by 1, 2 or 3 groups, which are identical ordifferent and selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy, or R^(e) and R^(f) orR^(3e) and R^(3f) together with the nitrogen atom, to which they arebound may form a 5-, 6 or 7-membered, saturated or unsaturated N-boundheterocyclic radical, which may carry as a ring member a furtherheteroatom selected from O, S and N and which is unsubstituted or maycarry 1, 2, 3 or 4 groups, which are identical or different and selectedfrom the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl andC₁-C₄-alkoxy.

More preferably R^(e), R^(f), R^(3e), R^(3f) independently of each otherare selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and benzyl, orR^(e) and R^(f) or R^(3e) and R^(3f) together with the nitrogen atom, towhich they are bound may form a 5- or 6-membered, saturated orunsaturated N-bound heterocyclic radical, which may carry as a ringmember a further heteroatom selected from O, S and N and which isunsubstituted or may carry 1, 2 or 3 groups, which are identical ordifferent and selected from the group consisting of halogen, C₁-C₄-alkyland C₁-C₄-haloalkyl.

In particular, R^(e), R^(f), R^(3e), R^(3f) independently of each otherare selected from hydrogen and C₁-C₄-alkyl, or R^(e) and R^(f) or R^(3e)and R^(3f) together with the nitrogen atom, to which they are bound mayform a 5- or 6-membered, saturated N-bound heterocyclic radical, whichmay carry as a ring member a further heteroatom selected from O, S and Nand which is unsubstituted or may carry 1, 2 or 3 methyl groups.

R^(g), R^(2g), R^(3g) independently of each other are selected fromhydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted orpartly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl.

More preferably R^(g), R^(2g), R^(3g) independently of each other areselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl andC₃-C₇-cycloalkyl, which is unsubstituted or partly or completelyhalogenated, and in particular selected from hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl andC₃-C₆-cycloalkyl.

R^(h), R^(2h), R^(3h) independently of each other are selected fromhydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted orpartly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl and a radical C(═O)—R^(k),where R^(k) is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenyl.

More preferably R^(h), R^(2h), R^(3h) independently of each other areselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl andC₃-C₇-cycloalkyl, which is unsubstituted or partly or completelyhalogenated, and in particular selected from hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl andC₃-C₆-cycloalkyl; or

R^(g) and R^(h) or R^(2g) and R^(2h) or R^(3g) and R^(3h) together withthe nitrogen atom, to which they are bound may form a 5-, 6 or7-membered, saturated or unsaturated N-bound heterocyclic radical, whichmay carry as a ring member a further heteroatom selected from O, S and Nand which is unsubstituted or may carry 1, 2, 3 or 4 groups, which areidentical or different and selected from the group consisting of ═O,halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl and C₁-C₄-alkoxy;

more preferably R^(g) and R^(h) or R^(2g) and R^(2h) or R^(3g) andR^(3h) together with the nitrogen atom, to which they are bound may forma 5- or 6-membered, saturated or unsaturated N-bound heterocyclicradical, which may carry as a ring member a further heteroatom selectedfrom O, S and N and which is unsubstituted or may carry 1, 2 or 3groups, which are identical or different and selected from the groupconsisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

and in particular, R^(g) and R^(h) or R^(2g) and R^(2h) or R^(3g) andR^(3h) together with the nitrogen atom, to which they are bound may forma 5- or 6-membered, saturated N-bound heterocyclic radical, which maycarry as a ring member a further heteroatom selected from O, S and N andwhich is unsubstituted or may carry 1, 2 or 3 methyl groups.

n and k independently of each other are 0 or 2, and in particular 2.

Examples of preferred compounds are the individual compounds compiled inthe Tables 1 to 3 below. Moreover, the meanings mentioned below for theindividual variables in the Tables are per se, independently of thecombination in which they are mentioned, a particularly preferredembodiment of the substituents in question.

Table 1 Compounds of the formula I in which R is methyl and thecombination of R¹, if present, CYC and R³, if present, for a compoundcorresponds in each case to one row of Table A;

Table 2 Compounds of the formula I in which R is ethyl and thecombination of R¹, if present, CYC and R³, if present, for a compoundcorresponds in each case to one row of Table A;

Table 3 Compounds of the formula I in which R is methoxy and thecombination of R¹, if present, CYC and R³, if present, for a compoundcorresponds in each case to one row of Table A.

TABLE A R¹ CYC R³ A-1 Cl Cyc-1a′-1 — A-2 Cl Cyc-1a′-2 — A-3 Cl Cyc-1a′-3— A-4 Cl Cyc-1a′-4 — A-5 Cl Cyc-1a′-5 — A-6 Cl Cyc-1a′-6 — A-7 ClCyc-1b′ — A-8 Cl Cyc-1c′ — A-9 Cl Cyc-1d′-1 — A-10 Cl Cyc-1d′-2 — A-11Cl Cyc-1d′-3 — A-12 Cl Cyc-1d′-4 — A-13 Cl Cyc-1d′-5 — A-14 Cl Cyc-1d′-6— A-15 Cl Cyc-1d′-7 — A-16 Cl Cyc-1d′-8 — A-17 Cl Cyc-1d′-9 — A-18 ClCyc-1e′ — A-19 Cl Cyc-1f′ — A-20 Cl Cyc-1f″-1 — A-21 Cl Cyc-1f″-2 — A-22Cl Cyc-1g′ — A-23 Cl Cyc-1h′-1 — A-24 Cl Cyc-1h′-2 — A-25 Cl Cyc-1h′-3 —A-26 Cl Cyc-1h′-4 — A-27 Cl Cyc-1h′-5 — A-28 CH₃ Cyc-1a′-1 — A-29 CH₃Cyc-1a′-2 — A-30 CH₃ Cyc-1a′-3 — A-31 CH₃ Cyc-1a′-4 — A-32 CH₃ Cyc-1a′-5— A-33 CH₃ Cyc-1a′-6 — A-34 CH₃ Cyc-1b′ — A-35 CH₃ Cyc-1c′ — A-36 CH₃Cyc-1d′-1 — A-37 CH₃ Cyc-1d′-2 — A-38 CH₃ Cyc-1d′-3 — A-39 CH₃ Cyc-1d′-4— A-40 CH₃ Cyc-1d′-5 — A-41 CH₃ Cyc-1d′-6 — A-42 CH₃ Cyc-1d′-7 — A-43CH₃ Cyc-1d′-8 — A-44 CH₃ Cyc-1d′-9 — A-45 CH₃ Cyc-1e′ — A-46 CH₃ Cyc-1f′— A-47 CH₃ Cyc-1f″-1 — A-48 CH₃ Cyc-1f″-2 — A-49 CH₃ Cyc-1g′ — A-50 CH₃Cyc-1h′-1 — A-51 CH₃ Cyc-1h′-2 — A-52 CH₃ Cyc-1h′-3 — A-53 CH₃ Cyc-1h′-4— A-54 CH₃ Cyc-1h′-5 — A-55 CF₃ Cyc-1a′-1 — A-56 CF₃ Cyc-1a′-2 — A-57CF₃ Cyc-1a′-3 — A-58 CF₃ Cyc-1a′-4 — A-59 CF₃ Cyc-1a′-5 — A-60 CF₃Cyc-1a′-6 — A-61 CF₃ Cyc-1b′ — A-62 CF₃ Cyc-1c′ — A-63 CF₃ Cyc-1d′-1 —A-64 CF₃ Cyc-1d′-2 — A-65 CF₃ Cyc-1d′-3 — A-66 CF₃ Cyc-1d′-4 — A-67 CF₃Cyc-1d′-5 — A-68 CF₃ Cyc-1d′-6 — A-69 CF₃ Cyc-1d′-7 — A-70 CF₃ Cyc-1d′-8— A-71 CF₃ Cyc-1d′-9 — A-72 CF₃ Cyc-1e′ — A-73 CF₃ Cyc-1f′ — A-74 CF₃Cyc-1f″-1 — A-75 CF₃ Cyc-1f″-2 — A-76 CF₃ Cyc-1g′ — A-77 CF₃ Cyc-1h′-1 —A-78 CF₃ Cyc-1h′-2 — A-79 CF₃ Cyc-1h′-3 — A-80 CF₃ Cyc-1h′-4 — A-81 CF₃Cyc-1h′-5 — A-82 SO₂CH₃ Cyc-1a′-1 — A-83 SO₂CH₃ Cyc-1a′-2 — A-84 SO₂CH₃Cyc-1a′-3 — A-85 SO₂CH₃ Cyc-1a′-4 — A-86 SO₂CH₃ Cyc-1a′-5 — A-87 SO₂CH₃Cyc-1a′-6 — A-88 SO₂CH₃ Cyc-1b′ — A-89 SO₂CH₃ Cyc-1c′ — A-90 SO₂CH₃Cyc-1d′-1 — A-91 SO₂CH₃ Cyc-1d′-2 — A-92 SO₂CH₃ Cyc-1d′-3 — A-93 SO₂CH₃Cyc-1d′-4 — A-94 SO₂CH₃ Cyc-1d′-5 — A-95 SO₂CH₃ Cyc-1d′-6 — A-96 SO₂CH₃Cyc-1d′-7 — A-97 SO₂CH₃ Cyc-1d′-8 — A-98 SO₂CH₃ Cyc-1d′-9 — A-99 SO₂CH₃Cyc-1e′ — A-100 SO₂CH₃ Cyc-1f′ — A-101 SO₂CH₃ Cyc-1f″-1 — A-102 SO₂CH₃Cyc-1f″-2 — A-103 SO₂CH₃ Cyc-1g′ — A-104 SO₂CH₃ Cyc-1h′-1 — A-105 SO₂CH₃Cyc-1h′-2 — A-106 SO₂CH₃ Cyc-1h′-3 — A-107 SO₂CH₃ Cyc-1h′-4 — A-108SO₂CH₃ Cyc-1h′-5 — A-109 — Cyc-2a′ F A-110 — Cyc-2b′ F A-111 — Cyc-2c′ FA-112 — Cyc-2d′ F A-113 — Cyc-2a′ Cl A-114 — Cyc-2b′ Cl A-115 — Cyc-2c′Cl A-116 — Cyc-2d′ Cl A-117 — Cyc-2a′ Br A-118 — Cyc-2b′ Br A-119 —Cyc-2c′ Br A-120 — Cyc-2d′ Br A-121 — Cyc-2a′ CH₃ A-122 — Cyc-2b′ CH₃A-123 — Cyc-2c′ CH₃ A-124 — Cyc-2d′ CH₃ A-125 — Cyc-2a′ CF₃ A-126 —Cyc-2b′ CF₃ A-127 — Cyc-2c′ CF₃ A-128 — Cyc-2d′ CF₃ A-129 — Cyc-2a′ OCH₃A-130 — Cyc-2b′ OCH₃ A-131 — Cyc-2c′ OCH₃ A-132 — Cyc-2d′ OCH₃

The compounds of the formula I can be prepared by standard methods oforganic chemistry, e.g. by the methods described hereinafter in schemes1 to 5. The substituents, variables and indices in schemes 1 to 5 are asdefined above for formula I, if not otherwise specified.

The compounds of formula I can be prepared for instance as shown in theScheme 1 below.

4-Amino-1,2,5-oxadiazole compounds of formula III can be reacted withbenzoyl derivatives of formula II to afford compounds of the formula I.Z is a leaving group, such as halogen, in particular Cl, an anhydrideresidue or an active ester residue. Especially in case of Z beinghalogen the reaction is suitably carried out in the presence of a base.Suitable bases are for example carbonates, such as lithium, sodium orpotassium carbonates, amines, such as trimethylamine or triethylamine,and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or2,4,6-trimethylpyridine. Suitable solvents are in particular aproticsolvents such as pentane, hexane, heptane, octane, cyclohexane,dichloromethane, chloroform, 1,2-dichlorethane, benzene, chlorobenzene,toluene, the xylenes, dichlorobenzene, trimethylbenzene, pyridine,2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethylether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyltert-butylether, 1,4-dioxane, N,N-dimethyl formamide, N-methylpyrrolidinone or mixtures thereof. The starting materials are generallyreacted with one another in equimolar or nearly equimolar amounts at areaction temperature usually in the range of −20° C. to 100° C. andpreferably in the range of −5° C. to 50° C.

Alternatively, compounds of formula I can also be prepared as shown inScheme 2. Reaction of a 4-amino-1,2,5-oxadiazole compound III with abenzoic acid derivative of formula IV yields compound I. The reaction ispreferably carried in the presence of a suitable activating agent whichconverts the acid group of compound IV into an activated ester or amide.For this purpose activating agents known in the art, such as1,1′,carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P)can be employed. The activated ester or amide can be formed, dependingin particular on the specific activating agent used, either in situ bycontacting compound IV with the activating agent in the presence ofcompound III, or in a separate step prior to the reaction with compoundIII. It may be advantageous, especially in cases where DCC or EDC areused as activating agent, to include further additives in the activatingreaction, such as hydroxybenzotriazole (HOBt), nitrophenol,pentafluorophenol, 2,4,5-trichlorophenol or N-hydroxysuccinimide. It mayfurther be advantageous to prepare the activated ester or amide in thepresence of a base, for example a tertiary amine. The activated ester oramide is either in situ or subsequently reacted with the amine offormula III to afford the amide of formula I. The reaction normallytakes place in anhydrous inert solvents, such as chlorinatedhydrocarbons, e.g. dichloromethane or dichloroethane, ethers, e.g.tetrahydrofuran or 1,4-dioxane or carboxamides, e.g.N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. Thereaction is ordinarily carried out at temperatures in the range from−20° C. to +25° C.

The compounds of formula II and their respective benzoic acid precursorsof formula IV can be obtained by purchase or can be prepared byprocesses known in the art or disclosed in the literature, e.g. in WO2000/020408, WO 2001/040176, WO 96/30368, WO 97/30986, DE 4428000, WO2002/048121 and WO 98/12192.

The 4-amino-1,2,5-oxadiazole compounds of the formula III are eithercommercially available or are obtainable according to methods known fromthe literature. For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can beprepared from β-ketoesters pursuant to a procedure described in RussianChemical Bulletin, Int. Ed., 54(4), 1032-1037 (2005), as depicted inScheme 3.

As shown in Scheme 4, the compounds of the formula III, where R ishalogen, can be prepared from commercially available3,4-diamino-1,2,5-oxadiazole according to procedures described in theliterature, e.g. by the Sandmeyer-type reaction disclosed in HeteroatomChemistry, 15(3), 199-207 (2004).

As shown in Scheme 5, the compounds of the formula III, where R is anucleophilic residue, can be prepared by introducing the nucleophilicresidue via the substitution of a leaving group L, e.g. halogene, in the4-position of the 1,2,5-oxadiazoles compounds of formula V in accordanceto precedures disclosed, for example in Journal of Chemical Research,Synopses (6), 190 (1985), in Izvestiya Akademii Nauk SSSR, SeriyaKhimicheskaya (9), 2086-8 (1986) or in Russian Chemical Bulletin(Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3),596-614 (2004).

As a rule, the compounds of formula I including their stereoisomers,salts, tautomers and N-oxides, and their precursors in the synthesisprocess, can be prepared by the methods described above. If individualcompounds can not be prepared via the above-described routes, they canbe prepared by derivatization of other compounds I or the respectiveprecursor or by customary modifications of the synthesis routesdescribed. For example, in individual cases, certain compounds offormula I can advantageously be prepared from other compounds of formulaI by derivatization, e.g. by ester hydrolysis, amidation,esterification, ether cleavage, olefination, reduction, oxidation andthe like, or by customary modifications of the synthesis routesdescribed.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor on silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ortrituration.

The compounds I and their agriculturally suitable salts are useful asherbicides. They are useful as such or as an appropriately formulatedcomposition. The herbicidal compositions comprising the compound I, inparticular the preferred aspects thereof, control vegetation on non-cropareas very efficiently, especially at high rates of application. Theyact against broad-leaved weeds and weed grasses in crops such as wheat,rice, corn, soybeans and cotton without causing any significant damageto the crop plants. This effect is mainly observed at low rates ofapplication.

Depending on the application method in question, the compounds I, inparticular the preferred aspects thereof, or compositions comprisingthem can additionally be employed in a further number of crop plants foreliminating unwanted plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified bybreeding, mutagenesis or genetic engineering. Genetically modifiedplants are plants whose genetic material has been modified in a mannerwhich does not occur under natural conditions by crossing, mutations ornatural recombination (i.e. reassembly of the genetic information).Here, in general, one or more genes are integrated into the geneticmaterial of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, bybreeding and genetic engineering, have acquired tolerance to certainclasses of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD)inhibitors, acetolactate synthase (ALS) inhibitors, such as, forexample, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) orimidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685,WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073),enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as,for example, glyphosate (see, for example, WO 92/00377), glutaminesynthetase (GS) inhibitors, such as, for example, glufosinate (see, forexample, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, forexample, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant toimidazolinones, for example imazamox, have been generated with the aidof classic breeding methods (mutagenesis). Crop plants such as soybeans,cotton, corn, beet and oilseed rape, resistant to glyphosate orglufosinate, which are available under the tradenames RoundupReady®(glyphosate) and Liberty Link® (glufosinate) have been generated withthe aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more toxins, for examplethose of the bacterial strain Bacillus ssp. Toxins which are produced bysuch genetically modified plants include, for example, insecticidalproteins of Bacillus spp., in particular B. thuringiensis, such as theendotoxins Cry1Ab, Cry1Ac, Cry1F, CrylFa2, Cry2Ab, Cry3A, Cry3Bb1,Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs),for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins ofnematode-colonizing bacteria, for example Photorhabdus spp. orXenorhabdus spp.; toxins of animal organisms, for example wasp, spideror scorpion toxins; fungal toxins, for example from Streptomycetes;plant lectins, for example from peas or barley; agglutinins; proteinaseinhibitors, for example trypsin inhibitors, serine protease inhibitors,patatin, cystatin or papain inhibitors, ribosome-inactivating proteins(RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin;steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase,ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysoneinhibitors, or HMG-CoA reductase; ion channel blockers, for exampleinhibitors of sodium channels or calcium channels; juvenile hormoneesterase; receptors of the diuretic hormone (helicokinin receptors);stilbene synthase, bibenzyl synthase, chitinases and glucanases. In theplants, these toxins may also be produced as pretoxins, hybrid proteinsor truncated or otherwise modified proteins. Hybrid proteins arecharacterized by a novel combination of different protein domains (see,for example, WO 2002/015701). Further examples of such toxins orgenetically modified plants which produce these toxins are disclosed inEP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO03/018810 and WO 03/052073. The methods for producing these geneticallymodified plants are known to the person skilled in the art anddisclosed, for example, in the publications mentioned above. Numerous ofthe toxins mentioned above bestow, upon the plants by which they areproduced, tolerance to pests from all taxonomic classes of arthropods,in particular to beetles (Coeleropta), dipterans (Diptera) andbutterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding forinsecticidal toxins are described, for example, in the publicationsmentioned above, and some of them are commercially available, such as,for example, YieldGard® (corn varieties producing the toxin Cry1Ab),YieldGard® Plus (corn varieties which produce the toxins Cry1Ab andCry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c),Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B(cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cottonvarieties which produce the toxin Cry1Ac), Bollgard® II (cottonvarieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cottonvarieties which produce a VIP toxin); NewLeaf® (potato varieties whichproduce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®,Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta SeedsSAS, France (corn varieties which produce the toxin Cry1Ab and the PATenzyme), MIR604 from Syngenta Seeds SAS, France (corn varieties whichproduce a modified version of the toxin Cry3A, see WO 03/018810), MON863 from Monsanto Europe S.A., Belgium (corn varieties which produce thetoxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cottonvarieties which produce a modified version of the toxin Cry1Ac) and 1507from Pioneer Overseas Corporation, Belgium (corn varieties which producethe toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with theaid of genetic engineering, produce one or more proteins which are morerobust or have increased resistance to bacterial, viral or fungalpathogens, such as, for example, pathogenesis-related proteins (PRproteins, see EP-A 0 392 225), resistance proteins (for example potatovarieties producing two resistance genes against Phytophthora infestansfrom the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (forexample potato cultivars which, by producing this protein, are resistantto bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whoseproductivity has been improved with the aid of genetic engineeringmethods, for example by enhancing the potential yield (for examplebiomass, grain yield, starch, oil or protein content), tolerance todrought, salt or other limiting environmental factors or resistance topests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have beenmodified with the aid of genetic engineering methods in particular forimproving human or animal diet, for example by oil plants producinghealth-promoting long-chain omega 3 fatty acids or monounsaturated omega9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modifiedwith the aid of genetic engineering methods for improving the productionof raw materials, for example by increasing the amylopectin content ofpotatoes (Amflora® potato).

Furthermore, it has been found that the compounds of the formula I arealso suitable for the defoliation and/or desiccation of plant parts, forwhich crop plants such as cotton, potato, oilseed rape, sunflower,soybean or field beans, in particular cotton, are suitable. In thisregard, there have been found compositions for the desiccation and/ordefoliation of plants, processes for preparing these compositions andmethods for desiccating and/or defoliating plants using the compounds ofthe formula I.

As desiccants, the compounds of the formula I are particularly suitablefor desiccating the above-ground parts of crop plants such as potato,oilseed rape, sunflower and soybean, but also cereals. This makespossible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is madepossible by concentrating within a certain period of time thedehiscence, or reduction of adhesion to the tree, in citrus fruit,olives and other species and varieties of pomaceous fruit, stone fruitand nuts. The same mechanism, i.e. the promotion of the development ofabscission tissue between fruit part or leaf part and shoot part of theplants is also essential for the readily controllable defoliation ofuseful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individualcotton plants mature leads to an increased fiber quality afterharvesting.

The compounds I, or the herbicidal compositions comprising the compoundsI, can be used, for example, in the form of ready-to-spray aqueoussolutions, powders, suspensions, also highly concentrated aqueous, oilyor other suspensions or dispersions, emulsions, oil dispersions, pastes,dusts, materials for broadcasting, or granules, by means of spraying,atomizing, dusting, spreading, watering or treatment of the seed ormixing with the seed. The use forms depend on the intended purpose; ineach case, they should ensure the finest possible distribution of theactive ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I, and auxiliaries which are customary for the formulation of cropprotection agents.

Examples of auxiliaries customary for the formulation of crop protectionagents are inert auxiliaries, solid carriers, surfactants (such asdispersants, protective colloids, emulsifiers, wetting agents andtackifiers), organic and inorganic thickeners, bactericides, antifreezeagents, antifoams, if appropriate colorants and, for seed formulations,adhesives.

Examples of thickeners (i.e. compounds which impart to the formulationmodified flow properties, i.e. high viscosity in the state of rest andlow viscosity in motion) are polysaccharides, such as xanthan gum(Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T.Vanderbilt), and also organic and inorganic sheet minerals, such asAttaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example,Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols,fatty acids, salts of fatty acids, organofluorine compounds and mixturesthereof.

Bactericides can be added for stabilizing the aqueous herbicidalformulation. Examples of bactericides are bactericides based ondiclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide®RS from Thor Chemie and Kathon® MK from Rohm & Haas), and alsoisothiazolinone derivates, such as alkylisothiazolinones andbenzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol,urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments andwater-soluble dyes. Examples which may be mentioned are the dyes knownunder the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1,and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2,pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13,pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1,pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25,basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate,polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate andmagnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersantsand also emulsifiers) are the alkali metal salts, alkaline earth metalsalts and ammonium salts of aromatic sulfonic acids, for examplelignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonicacids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) anddibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fattyacids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols, and also of fatty alcohol glycol ethers, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of the naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignosulfite wasteliquors and proteins, denatured proteins, polysaccharides (e.g.methylcellulose), hydrophobically modified starches, polyvinyl alcohol(Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types),polyalkoxylates, polyvinylamine (BASF SE, Lupamine types),polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone andcopolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thecompounds of the formula I or Ia, either as such or dissolved in an oilor solvent, can be homogenized in water by means of a wetting agent,tackifier, dispersant or emulsifier. Alternatively, it is also possibleto prepare concentrates comprising active substance, wetting agent,tackifier, dispersant or emulsifier and, if desired, solvent or oil,which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from 0.001 to 98% by weight, preferably 0.01 to95% by weight of at least one active compound. The active compounds areemployed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The formulations or ready-to-use preparations may also comprise acids,bases or buffer systems, suitable examples being phosphoric acid orsulfuric acid, or urea or ammonia.

The compounds I of the invention can for example be formulated asfollows:

1. Products for Dilution with Water

A Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts byweight of water or a water-soluble solvent. As an alternative, wettersor other adjuvants are added. The active compound dissolves upondilution with water. This gives a formulation with an active compoundcontent of 10% by weight.

B Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts byweight of cyclohexanone with addition of 10 parts by weight of adispersant, for example polyvinylpyrrolidone. Dilution with water givesa dispersion. The active compound content is 20% by weight.

C Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). Dilution with water gives an emulsion. Theformulation has an active compound content of 15% by weight.

D Emulsions

25 parts by weight of active compound are dissolved in 35 parts byweight of an organic solvent (e.g. alkylaromatics) with addition ofcalcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case5 parts by weight). This mixture is introduced into 30 parts by weightof water by means of an emulsifier (e.g. Ultraturrax) and made into ahomogeneous emulsion. Dilution with water gives an emulsion. Theformulation has an active compound content of 25% by weight.

E Suspensions

In an agitated ball mill, 20 parts by weight of active compound arecomminuted with addition of 10 parts by weight of dispersants andwetters and 70 parts by weight of water or an organic solvent to give afine active compound suspension. Dilution with water gives a stablesuspension of the active compound. The active compound content in theformulation is 20% by weight.

F Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of50 parts by weight of dispersants and wetters and made intowater-dispersible or water-soluble granules by means of technicalappliances (for example extrusion, spray tower, fluidized bed). Dilutionwith water gives a stable dispersion or solution of the active compound.The formulation has an active compound content of 50% by weight.

G Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator millwith addition of 25 parts by weight of dispersants, wetters and silicagel. Dilution with water gives a stable dispersion or solution of theactive compound. The active compound content of the formulation is 75%by weight.

H Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts byweight of dispersant, 1 part by weight of gelling agent and 70 parts byweight of water or of an organic solvent are ground to give a finesuspension. Dilution with water gives a stable suspension with activecompound content of 20% by weight.

2. Products to be Applied Undiluted

I Dusts

5 parts by weight of active compound are ground finely and mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dusting powder with an active compound content of 5% by weight.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associatedwith 99.5 parts by weight of carriers. Current methods here areextrusion, spray-drying or the fluidized bed. This gives granules to beapplied undiluted with an active compound content of 0.5% by weight.

K ULV Solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts byweight of an organic solvent, for example xylene. This gives a productto be applied undiluted with an active compound content of 10% byweight.

The compounds I or the herbicidal compositions comprising them can beapplied pre- or post-emergence, or together with the seed of a cropplant. It is also possible to apply the herbicidal compositions oractive compounds by applying seed, pretreated with the herbicidalcompositions or active compounds, of a crop plant. If the activecompounds are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spraying equipment, in such a way that as far aspossible they do not come into contact with the leaves of the sensitivecrop plants, while the active compounds reach the leaves of undesirableplants growing underneath, or the bare soil surface (post-directed,lay-by).

In a further embodiment, the compounds of the formula I or theherbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar tothe person skilled in the art (seed dressing, seed coating, seeddusting, seed soaking, seed film coating, seed multilayer coating, seedencrusting, seed dripping and seed pelleting) based on the compounds ofthe formula I according to the invention or the compositions preparedtherefrom. Here, the herbicidal compositions can be applied diluted orundiluted.

The term seed comprises seed of all types, such as, for example, corns,seeds, fruits, tubers, cuttings and similar forms. Here, preferably, theterm seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but alsothe seed of transgenic plants or plants obtained by customary breedingmethods.

The rates of application of active compound are from 0.001 to 3.0,preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending onthe control target, the season, the target plants and the growth stage.To treat the seed, the compounds I are generally employed in amounts offrom 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I incombination with safeners. Safeners are chemical compounds which preventor reduce damage to useful plants without substantially affecting theherbicidal action of the compounds of the formula I on unwanted plants.They can be used both before sowing (for example in the treatment ofseed, or on cuttings or seedlings) and before or after the emergence ofthe useful plant. The safeners and the compounds of the formula I can beused simultaneously or in succession. Suitable safeners are, forexample, (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenone oximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids,phosphorothiolates and O-phenyl N-alkylcarbamates and theiragriculturally useful salts and, provided that they have an acidfunction, their agriculturally useful derivatives, such as amides,esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, thecompounds of the formula I can be mixed and jointly applied withnumerous representatives of other herbicidal or growth-regulating groupsof active compounds or with safeners. Suitable mixing partners are, forexample, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoricacid and its derivatives, aminotriazoles, anilides,aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acidand its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinoline carboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivates, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- andheteroaryloxyphenoxypropionic esters, phenylacetic acid and itsderivatives, 2-phenyl-propionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides, uracils and alsophenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds I alone or incombination with other herbicides or else also mixed with further cropprotection agents, jointly, for example with compositions forcontrolling pests or phytopathogenic fungi or bacteria. Also of interestis the miscibility with mineral salt solutions which are employed foralleviating nutritional and trace element deficiencies. Other additivessuch as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with thepyridine compounds of the formula I according to the present inventionare:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop,clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop,diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P,fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop,quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim,tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate,EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb,pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate andvernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl,bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl,chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl,cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone,flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron,metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron,penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone,propoxycarbazone-sodium, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid,pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium,pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,trifloxysulfuron, triflusulfuron, triflusulfuron-methyl andtritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil,bromofenoxim, bromoxynil and its salts and esters, chlorobromuron,chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham,desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron,fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon,isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron,metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat,paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor,phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn,thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin,2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)-methylsulfamoyl]benzamide(H-1; CAS 372137-35-4),ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(H-2; CAS 353292-31-6),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-3; CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-4; CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-5; CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(H-6; CAS 45100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione,2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dioneand1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone,diflufenican, fluridone, flurochloridone, flurtamone, isoxaflutole,mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone,4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one(H-7; CAS 352010-68-5) and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8;CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium(sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate andglufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin,carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine,dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor,dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet,mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide,napropamide, pethoxamid, piperophos, pretilachlor, propachlor,propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings:

-   Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset,    which radicals may be substituted by one to three groups R^(aa);    R²¹, R²², R²³, R²⁴ are hydrogen, halogen or C₁-C₄-alkyl; X is O or    NH; N is 0 or 1.

Compounds of the formula 2 have in particular the following meanings:

Y is

where # denotes the bond to the skeleton of the molecule; and

R²¹, R²², R²³, R²⁴ are hydrogen, Cl, F or CH₃; R²⁵ is halogen,C₁-C₄-alkyl or C₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁸ is hydrogen, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; Nis 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

Y is

R²¹ is H; R²², R²³ are F; R²⁴ is hydrogen or F; X is oxygen; N is 0 or1.

Particularly preferred compounds of the formula 2 are:

3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane-sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-1);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-2);4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-3);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-4);4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-5);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole(2-6);4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-7);3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole(2-8);4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole(2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters,aminopyralid and its salts such asaminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorprop and its salts and esters, dichlorprop-P and its salts andesters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA andits salts and esters, MCPA-thioethyl, MCPB and its salts and esters,mecoprop and its salts and esters, mecoprop-P and its salts and esters,picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6)and its salts and esters, triclopyr and its salts and esters, and5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet,difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron,endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol,flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan,maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide,methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone,pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are knownherbicides and safeners, see, for example, The Compendium of PesticideCommon Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke,R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart,1995. Further herbicidally active compounds are known from WO 96/26202,WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991and from W. Kramer et al. (ed.) “Modern Crop Protection Compounds”, Vol.1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a cropprotection composition formulated as a 1-component compositioncomprising an active compound combination comprising at least onepyridine compound of the formula I and at least one further activecompound, preferably selected from the active compounds of groups b1 tob15, and at least one solid or liquid carrier and/or one or moresurfactants and, if desired, one or more further auxiliaries customaryfor crop protection compositions. The invention also relates tocompositions in the form of a crop protection composition formulated asa 2-component composition comprising a first component comprising atleast one pyridine compound of the formula I, a solid or liquid carrierand/or one or more surfactants and a second component comprising atleast one further active compound selected from the active compounds ofgroups b1 to b15, a solid or liquid carrier and/or one or moresurfactants, where additionally both components may also comprisefurther auxiliaries customary for crop protection compositions.

In binary compositions comprising at least one compound of the formula Ias component A and at least one herbicide B, the weight ratio of theactive compounds A:B is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula Ias component A and at least one safener C, the weight ratio of theactive compounds A:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1.

In ternary compositions comprising both at least one compound of theformula I as component A, at least one herbicide B and at least onesafener C, the relative parts by weight of the components A:B aregenerally in the range of from 1:1000 to 1000:1, preferably in the rangeof from 1:500 to 500:1, in particular in the range of from 1:250 to250:1 and particularly preferably in the range of from 1:75 to 75:1; theweight ratio of the components A:C is generally in the range of from1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, inparticular in the range of from 1:250 to 250:1 and particularlypreferably in the range of from 1:75 to 75:1; and the weight ratio ofthe components B:C is generally in the range of from 1:1000 to 1000:1,preferably in the range of from 1:500 to 500:1, in particular in therange of from 1:250 to 250:1 and particularly preferably in the range offrom 1:75 to 75:1. Preferably, the weight ratio of the components A+B tothe component C is in the range of from 1:500 to 500:1, in particular inthe range of from 1:250 to 250:1 and particularly preferably in therange of from 1:75 to 75:1.

Examples of particularly preferred compositions according to theinvention comprising in each case one individualized compound of theformula I and one mixing partner or a mixing partner combination aregiven in Table B below.

A further aspect of the invention relates to the compositions B-1 toB-1236 listed in Table B below, where in each case one row of Table Bcorresponds to a herbicidal composition comprising one of the compoundsof the formula I individualized in the above description (component 1)and the further active compound from groups b1) to b15) and/or safener Cstated in each case in the row in question (component 2). The activecompounds in the compositions described are in each case preferablypresent in synergistically effective amounts.

TABLE B Herbicide(s) B Safener C B-1 clodinafop-propargyl — B-2cycloxydim — B-3 cyhalofop-butyl — B-4 fenoxaprop-P-ethyl — B-5pinoxaden — B-6 profoxydim — B-7 tepraloxydim — B-8 tralkoxydim — B-9esprocarb — B-10 prosulfocarb — B-11 thiobencarb — B-12 triallate — B-13bensulfuron-methyl — B-14 bispyribac-sodium — B-15 cyclosulfamuron —B-16 flumetsulam — B-17 flupyrsulfuron-methyl-sodium — B-18foramsulfuron — B-19 imazamox — B-20 imazapic — B-21 imazapyr — B-22imazaquin — B-23 imazethapyr — B-24 imazosulfuron — B-25iodosulfuron-methyl-sodium — B-26 mesosulfuron — B-27 nicosulfuron —B-28 penoxsulam — B-29 propoxycarbazone-sodium — B-30pyrazosulfuron-ethyl — B-31 pyroxsulam — B-32 rimsulfuron — B-33sulfosulfuron — B-34 thiencarbazone-methyl — B-35 tritosulfuron — B-362,4-D and its salts and esters — B-37 aminopyralid and its salts andesters — B-38 clopyralid and its salts and esters — B-39 dicamba and itssalts and esters — B-40 fluroxypyr-meptyl — B-41 quinclorac — B-42quinmerac — B-43 H-9 — B-44 diflufenzopyr — B-45 diflufenzopyr-sodium —B-46 clomazone — B-47 diflufenican — B-48 fluorochloridone — B-49isoxaflutol — B-50 mesotrione — B-51 picolinafen — B-52 sulcotrione —B-53 tefuryltrione — B-54 tembotrione — B-55 topramezone — B-56 H-7 —B-57 atrazine — B-58 diuron — B-59 fluometuron — B-60 hexazinone — B-61isoproturon — B-62 metribuzin — B-63 propanil — B-64 terbuthylazine —B-65 paraquat dichloride — B-66 flumioxazin — B-67 oxyfluorfen — B-68saflufenacil — B-69 sulfentrazone — B-70 H-1 — B-71 H-2 — B-72glyphosate — B-73 glyphosate-isopropylammonium — B-74glyphosate-trimesium (sulfosate) — B-75 glufosinate — B-76glufosinate-ammonium — B-77 pendimethalin — B-78 trifluralin — B-79acetochlor — B-80 cafenstrole — B-81 dimethenamid-P — B-82 fentrazamide— B-83 flufenacet — B-84 mefenacet — B-85 metazachlor — B-86metolachlor-S — B-87 pyroxasulfone — B-88 isoxaben — B-89 dymron — B-90indanofan — B-91 oxaziclomefone — B-92 triaziflam — B-93 chlorotoluron —B-94 atrazine + H-1 — B-95 atrazine + glyphosate — B-96 atrazine +mesotrione — B-97 atrazine + nicosulfuron — B-98 atrazine + tembotrione— B-99 atrazine + topramezone — B-100 clomazone + glyphosate — B-101diflufenican + clodinafop-propargyl — B-102 diflufenican +fenoxaprop-P-ethyl — B-103 diflufenican + flupyrsulfuron-methyl-sodium —B-104 diflufenican + glyphosate — B-105 diflufenican +mesosulfuron-methyl — B-106 diflufenican + pinoxaden — B-107diflufenican + pyroxsulam — B-108 flumetsulam + glyphosate — B-109flumioxazin + glyphosate — B-110 imazapic + glyphosate — B-111imazethapyr + glyphosate — B-112 isoxaflutol + H-1 — B-113 isoxaflutol +glyphosate — B-114 metazachlor + H-1 — B-115 metazachlor + glyphosate —B-116 metazachlor + mesotrione — B-117 metazachlor + nicosulfuron —B-118 metazachlor + terbuthylazine — B-119 metazachlor + topramezone —B-120 metribuzin + glyphosate — B-121 pendimethalin + H-1 — B-122pendimethalin + clodinafop-propargyl — B-123 pendimethalin +fenoxaprop-P-ethyl — B-124 pendimethalin + flupyrsulfuron-methyl-sodium— B-125 pendimethalin + glyphosate — B-126 pendimethalin +mesosulfuron-methyl — B-127 pendimethalin + mesotrione — B-128pendimethalin + nicosulfuron — B-129 pendimethalin + pinoxaden — B-130pendimethalin + pyroxsulam — B-131 pendimethalin + tembotrione — B-132pendimethalin + topramezone — B-133 pyroxasulfone + tembotrione — B-134pyroxasulfone + topramezone — B-135 sulfentrazone + glyphosate — B-136terbuthylazine + H-1 — B-137 terbuthylazine + foramsulfuron — B-138terbuthylazine + glyphosate — B-139 terbuthylazine + mesotrione — B-140terbuthylazine + nicosulfuron — B-141 terbuthylazine + tembotrione —B-142 terbuthylazine + topramezone — B-143 trifluralin + glyphosate —B-144 — benoxacor B-145 — cloquintocet B-146 — cyprosulfamide B-147 —dichlormid B-148 — fenchlorazole B-149 — isoxadifen B-150 — mefenpyrB-151 — H-11 B-152 — H-12 B-153 clodinafop-propargyl benoxacor B-154cycloxydim benoxacor B-155 cyhalofop-butyl benoxacor B-156fenoxaprop-P-ethyl benoxacor B-157 pinoxaden benoxacor B-158 profoxydimbenoxacor B-159 tepraloxydim benoxacor B-160 tralkoxydim benoxacor B-161esprocarb benoxacor B-162 prosulfocarb benoxacor B-163 thiobencarbbenoxacor B-164 triallate benoxacor B-165 bensulfuron-methyl benoxacorB-166 bispyribac-sodium benoxacor B-167 cyclosulfamuron benoxacor B-168flumetsulam benoxacor B-169 flupyrsulfuron-methyl-sodium benoxacor B-170foramsulfuron benoxacor B-171 imazamox benoxacor B-172 imazapicbenoxacor B-173 imazapyr benoxacor B-174 imazaquin benoxacor B-175imazethapyr benoxacor B-176 imazosulfuron benoxacor B-177iodosulfuron-methyl-sodium benoxacor B-178 mesosulfuron benoxacor B-179nicosulfuron benoxacor B-180 penoxsulam benoxacor B-181propoxycarbazone-sodium benoxacor B-182 pyrazosulfuron-ethyl benoxacorB-183 pyroxsulam benoxacor B-184 rimsulfuron benoxacor B-185sulfosulfuron benoxacor B-186 thiencarbazone-methyl benoxacor B-187tritosulfuron benoxacor B-188 2,4-D and its salts and esters benoxacorB-189 aminopyralid and its salts and esters benoxacor B-190 clopyralidand its salts and esters benoxacor B-191 dicamba and its salts andesters benoxacor B-192 fluroxypyr-meptyl benoxacor B-193 quincloracbenoxacor B-194 quinmerac benoxacor B-195 H-9 benoxacor B-196diflufenzopyr benoxacor B-197 diflufenzopyr-sodium benoxacor B-198clomazone benoxacor B-199 diflufenican benoxacor B-200 fluorochloridonebenoxacor B-201 isoxaflutol benoxacor B-202 mesotrione benoxacor B-203picolinafen benoxacor B-204 sulcotrione benoxacor B-205 tefuryltrionebenoxacor B-206 tembotrione benoxacor B-207 topramezone benoxacor B-208H-7 benoxacor B-209 atrazine benoxacor B-210 diuron benoxacor B-211fluometuron benoxacor B-212 hexazinone benoxacor B-213 isoproturonbenoxacor B-214 metribuzin benoxacor B-215 propanil benoxacor B-216terbuthylazine benoxacor B-217 paraquat dichloride benoxacor B-218flumioxazin benoxacor B-219 oxyfluorfen benoxacor B-220 saflufenacilbenoxacor B-221 sulfentrazone benoxacor B-222 H-1 benoxacor B-223 H-2benoxacor B-224 glyphosate benoxacor B-225 glyphosate-isopropylammoniumbenoxacor B-226 glyphosate-trimesium (sulfosate) benoxacor B-227glufosinate benoxacor B-228 glufosinate-ammonium benoxacor B-229pendimethalin benoxacor B-230 trifluralin benoxacor B-231 acetochlorbenoxacor B-232 cafenstrole benoxacor B-233 dimethenamid-P benoxacorB-234 fentrazamide benoxacor B-235 flufenacet benoxacor B-236 mefenacetbenoxacor B-237 metazachlor benoxacor B-238 metolachlor-S benoxacorB-239 pyroxasulfone benoxacor B-240 isoxaben benoxacor B-241 dymronbenoxacor B-242 indanofan benoxacor B-243 oxaziclomefone benoxacor B-244triaziflam benoxacor B-245 atrazine + H-1 benoxacor B-246 atrazine +glyphosate benoxacor B-247 atrazine + mesotrione benoxacor B-248atrazine + nicosulfuron benoxacor B-249 atrazine + tembotrione benoxacorB-250 atrazine + topramezone benoxacor B-251 clomazone + glyphosatebenoxacor B-252 diflufenican + clodinafop-propargyl benoxacor B-253diflufenican + fenoxaprop-P-ethyl benoxacor B-254 diflufenican +flupyrsulfuron-methyl-sodium benoxacor B-255 diflufenican + glyphosatebenoxacor B-256 diflufenican + mesosulfuron-methyl benoxacor B-257diflufenican + pinoxaden benoxacor B-258 diflufenican + pyroxsulambenoxacor B-259 flumetsulam + glyphosate benoxacor B-260 flumioxazin +glyphosate benoxacor B-261 imazapic + glyphosate benoxacor B-262imazethapyr + glyphosate benoxacor B-263 isoxaflutol + H-1 benoxacorB-264 isoxaflutol + glyphosate benoxacor B-265 metazachlor + H-1benoxacor B-266 metazachlor + glyphosate benoxacor B-267 metazachlor +mesotrione benoxacor B-268 metazachlor + nicosulfuron benoxacor B-269metazachlor + terbuthylazine benoxacor B-270 metazachlor + topramezonebenoxacor B-271 metribuzin + glyphosate benoxacor B-272 pendimethalin +H-1 benoxacor B-273 pendimethalin + clodinafop-propargyl benoxacor B-274pendimethalin + fenoxaprop-P-ethyl benoxacor B-275 pendimethalin +flupyrsulfuron-methyl-sodium benoxacor B-276 pendimethalin + glyphosatebenoxacor B-277 pendimethalin + mesosulfuron-methyl benoxacor B-278pendimethalin + mesotrione benoxacor B-279 pendimethalin + nicosulfuronbenoxacor B-280 pendimethalin + pinoxaden benoxacor B-281pendimethalin + pyroxsulam benoxacor B-282 pendimethalin + tembotrionebenoxacor B-283 pendimethalin + topramezone benoxacor B-284pyroxasulfone + tembotrione benoxacor B-285 pyroxasulfone + topramezonebenoxacor B-286 sulfentrazone + glyphosate benoxacor B-287terbuthylazine + H-1 benoxacor B-288 terbuthylazine + foramsulfuronbenoxacor B-289 terbuthylazine + glyphosate benoxacor B-290terbuthylazine + mesotrione benoxacor B-291 terbuthylazine +nicosulfuron benoxacor B-292 terbuthylazine + tembotrione benoxacorB-293 terbuthylazine + topramezone benoxacor B-294 trifluralin +glyphosate benoxacor B-295 clodinafop-propargyl cloquintocet B-296cycloxydim cloquintocet B-297 cyhalofop-butyl cloquintocet B-298fenoxaprop-P-ethyl cloquintocet B-299 pinoxaden cloquintocet B-300profoxydim cloquintocet B-301 tepraloxydim cloquintocet B-302tralkoxydim cloquintocet B-303 esprocarb cloquintocet B-304 prosulfocarbcloquintocet B-305 thiobencarb cloquintocet B-306 triallate cloquintocetB-307 bensulfuron-methyl cloquintocet B-308 bispyribac-sodiumcloquintocet B-309 cyclosulfamuron cloquintocet B-310 flumetsulamcloquintocet B-311 flupyrsulfuron-methyl-sodium cloquintocet B-312foramsulfuron cloquintocet B-313 imazamox cloquintocet B-314 imazapiccloquintocet B-315 imazapyr cloquintocet B-316 imazaquin cloquintocetB-317 imazethapyr cloquintocet B-318 imazosulfuron cloquintocet B-319iodosulfuron-methyl-sodium cloquintocet B-320 mesosulfuron cloquintocetB-321 nicosulfuron cloquintocet B-322 penoxsulam cloquintocet B-323propoxycarbazone-sodium cloquintocet B-324 pyrazosulfuron-ethylcloquintocet B-325 pyroxsulam cloquintocet B-326 rimsulfuroncloquintocet B-327 sulfosulfuron cloquintocet B-328thiencarbazone-methyl cloquintocet B-329 tritosulfuron cloquintocetB-330 2,4-D and its salts and esters cloquintocet B-331 aminopyralid andits salts and esters cloquintocet B-332 clopyralid and its salts andesters cloquintocet B-333 dicamba and its salts and esters cloquintocetB-334 fluroxypyr-meptyl cloquintocet B-335 quinclorac cloquintocet B-336quinmerac cloquintocet B-337 H-9 cloquintocet B-338 diflufenzopyrcloquintocet B-339 diflufenzopyr-sodium cloquintocet B-340 clomazonecloquintocet B-341 diflufenican cloquintocet B-342 fluorochloridonecloquintocet B-343 isoxaflutol cloquintocet B-344 mesotrionecloquintocet B-345 picolinafen cloquintocet B-346 sulcotrionecloquintocet B-347 tefuryltrione cloquintocet B-348 tembotrionecloquintocet B-349 topramezone cloquintocet B-350 H-7 cloquintocet B-351atrazine cloquintocet B-352 diuron cloquintocet B-353 fluometuroncloquintocet B-354 hexazinone cloquintocet B-355 isoproturoncloquintocet B-356 metribuzin cloquintocet B-357 propanil cloquintocetB-358 terbuthylazine cloquintocet B-359 paraquat dichloride cloquintocetB-360 flumioxazin cloquintocet B-361 oxyfluorfen cloquintocet B-362saflufenacil cloquintocet B-363 sulfentrazone cloquintocet B-364 H-1cloquintocet B-365 H-2 cloquintocet B-366 glyphosate cloquintocet B-367glyphosate-isopropylammonium cloquintocet B-368 glyphosate-trimesium(sulfosate) cloquintocet B-369 glufosinate cloquintocet B-370glufosinate-ammonium cloquintocet B-371 pendimethalin cloquintocet B-372trifluralin cloquintocet B-373 acetochlor cloquintocet B-374 cafenstrolecloquintocet B-375 dimethenamid-P cloquintocet B-376 fentrazamidecloquintocet B-377 flufenacet cloquintocet B-378 mefenacet cloquintocetB-379 metazachlor cloquintocet B-380 metolachlor-S cloquintocet B-381pyroxasulfone cloquintocet B-382 isoxaben cloquintocet B-383 dymroncloquintocet B-384 indanofan cloquintocet B-385 oxaziclomefonecloquintocet B-386 triaziflam cloquintocet B-387 atrazine + H-1cloquintocet B-388 atrazine + glyphosate cloquintocet B-389 atrazine +mesotrione cloquintocet B-390 atrazine + nicosulfuron cloquintocet B-391atrazine + tembotrione cloquintocet B-392 atrazine + topramezonecloquintocet B-393 clomazone + glyphosate cloquintocet B-394diflufenican + clodinafop-propargyl cloquintocet B-395 diflufenican +fenoxaprop-p-ethyl cloquintocet B-396 diflufenican +flupyrsulfuron-methyl-sodium cloquintocet B-397 diflufenican +glyphosate cloquintocet B-398 diflufenican + mesosulfuron-methylcloquintocet B-399 diflufenican + pinoxaden cloquintocet B-400diflufenican + pyroxsulam cloquintocet B-401 flumetsulam + glyphosatecloquintocet B-402 flumioxazin + glyphosate cloquintocet B-403imazapic + glyphosate cloquintocet B-404 imazethapyr + glyphosatecloquintocet B-405 isoxaflutol + H-1 cloquintocet B-406 isoxaflutol +glyphosate cloquintocet B-407 metazachlor + H-1 cloquintocet B-408metazachlor + glyphosate cloquintocet B-409 metazachlor + mesotrionecloquintocet B-410 metazachlor + nicosulfuron cloquintocet B-411metazachlor + terbuthylazine cloquintocet B-412 metazachlor +topramezone cloquintocet B-413 metribuzin + glyphosate cloquintocetB-414 pendimethalin + H-1 cloquintocet B-415 pendimethalin +clodinafop-propargyl cloquintocet B-416 pendimethalin +fenoxaprop-P-ethyl cloquintocet B-417 pendimethalin +flupyrsulfuron-methyl-sodium cloquintocet B-418 pendimethalin +glyphosate cloquintocet B-419 pendimethalin + mesosulfuron-methylcloquintocet B-420 pendimethalin + mesotrione cloquintocet B-421pendimethalin + nicosulfuron cloquintocet B-422 pendimethalin +pinoxaden cloquintocet B-423 pendimethalin + pyroxsulam cloquintocetB-424 pendimethalin + tembotrione cloquintocet B-425 pendimethalin +topramezone cloquintocet B-426 pyroxasulfone + tembotrione cloquintocetB-427 pyroxasulfone + topramezone cloquintocet B-428 sulfentrazone +glyphosate cloquintocet B-429 terbuthylazine + H-1 cloquintocet B-430terbuthylazine + foramsulfuron cloquintocet B-431 terbuthylazine +glyphosate cloquintocet B-432 terbuthylazine + mesotrione cloquintocetB-433 terbuthylazine + nicosulfuron cloquintocet B-434 terbuthylazine +tembotrione cloquintocet B-435 terbuthylazine + topramezone cloquintocetB-436 trifluralin + glyphosate cloquintocet B-437 clodinafop-propargyldichlormid B-438 cycloxydim dichlormid B-439 cyhalofop-butyl dichlormidB-440 fenoxaprop-P-ethyl dichlormid B-441 pinoxaden dichlormid B-442profoxydim dichlormid B-443 tepraloxydim dichlormid B-444 tralkoxydimdichlormid B-445 esprocarb dichlormid B-446 prosulfocarb dichlormidB-447 thiobencarb dichlormid B-448 triallate dichlormid B-449bensulfuron-methyl dichlormid B-450 bispyribac-sodium dichlormid B-451cyclosulfamuron dichlormid B-452 flumetsulam dichlormid B-453flupyrsulfuron-methyl-sodium dichlormid B-454 foramsulfuron dichlormidB-455 imazamox dichlormid B-456 imazapic dichlormid B-457 imazapyrdichlormid B-458 imazaquin dichlormid B-459 imazethapyr dichlormid B-460imazosulfuron dichlormid B-461 iodosulfuron-methyl-sodium dichlormidB-462 mesosulfuron dichlormid B-463 nicosulfuron dichlormid B-464penoxsulam dichlormid B-465 propoxycarbazone-sodium dichlormid B-466pyrazosulfuron-ethyl dichlormid B-467 pyroxsulam dichlormid B-468rimsulfuron dichlormid B-469 sulfosulfuron dichlormid B-470thiencarbazone-methyl dichlormid B-471 tritosulfuron dichlormid B-4722,4-D and its salts and esters dichlormid B-473 aminopyralid and itssalts and esters dichlormid B-474 clopyralid and its salts and estersdichlormid B-475 dicamba and its salts and esters dichlormid B-476fluroxypyr-meptyl dichlormid B-477 quinclorac dichlormid B-478 quinmeracdichlormid B-479 H-9 dichlormid B-480 diflufenzopyr dichlormid B-481diflufenzopyr-sodium dichlormid B-482 clomazone dichlormid B-483diflufenican dichlormid B-484 fluorochloridone dichlormid B-485isoxaflutol dichlormid B-486 mesotrione dichlormid B-487 picolinafendichlormid B-488 sulcotrione dichlormid B-489 tefuryltrione dichlormidB-490 tembotrione dichlormid B-491 topramezone dichlormid B-492 H-7dichlormid B-493 atrazine dichlormid B-494 diuron dichlormid B-495fluometuron dichlormid B-496 hexazinone dichlormid B-497 isoproturondichlormid B-498 metribuzin dichlormid B-499 propanil dichlormid B-500terbuthylazine dichlormid B-501 paraquat dichloride dichlormid B-502flumioxazin dichlormid B-503 oxyfluorfen dichlormid B-504 saflufenacildichlormid B-505 sulfentrazone dichlormid B-506 H-1 dichlormid B-507 H-2dichlormid B-508 glyphosate dichlormid B-509glyphosate-isopropylammonium dichlormid B-510 glyphosate-trimesium(sulfosate) dichlormid B-511 glufosinate dichlormid B-512glufosinate-ammonium dichlormid B-513 pendimethalin dichlormid B-514trifluralin dichlormid B-515 acetochlor dichlormid B-516 cafenstroledichlormid B-517 dimethenamid-P dichlormid B-518 fentrazamide dichlormidB-519 flufenacet dichlormid B-520 mefenacet dichlormid B-521 metazachlordichlormid B-522 metolachlor-S dichlormid B-523 pyroxasulfone dichlormidB-524 isoxaben dichlormid B-525 dymron dichlormid B-526 indanofandichlormid B-527 oxaziclomefone dichlormid B-528 triaziflam dichlormidB-529 atrazine + H-1 dichlormid B-530 atrazine + glyphosate dichlormidB-531 atrazine + mesotrione dichlormid B-532 atrazine + nicosulfurondichlormid B-533 atrazine + tembotrione dichlormid B-534 atrazine +topramezone dichlormid B-535 clomazone + glyphosate dichlormid B-536diflufenican + clodinafop-propargyl dichlormid B-537 diflufenican +fenoxaprop-p-ethyl dichlormid B-538 diflufenican +flupyrsulfuron-methyl-sodium dichlormid B-539 diflufenican + glyphosatedichlormid B-540 diflufenican + mesosulfuron-methyl dichlormid B-541diflufenican + pinoxaden dichlormid B-542 diflufenican + pyroxsulamdichlormid B-543 flumetsulam + glyphosate dichlormid B-544 flumioxazin +glyphosate dichlormid B-545 imazapic + glyphosate dichlormid B-546imazethapyr + glyphosate dichlormid B-547 isoxaflutol + H-1 dichlormidB-548 isoxaflutol + glyphosate dichlormid B-549 metazachlor + H-1dichlormid B-550 metazachlor + glyphosate dichlormid B-551 metazachlor +mesotrione dichlormid B-552 metazachlor + nicosulfuron dichlormid B-553metazachlor + terbuthylazine dichlormid B-554 metazachlor + topramezonedichlormid B-555 metribuzin + glyphosate dichlormid B-556pendimethalin + H-1 dichlormid B-557 pendimethalin +clodinafop-propargyl dichlormid B-558 pendimethalin + fenoxaprop-P-ethyldichlormid B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormidB-560 pendimethalin + glyphosate dichlormid B-561 pendimethalin +mesosulfuron-methyl dichlormid B-562 pendimethalin + mesotrionedichlormid B-563 pendimethalin + nicosulfuron dichlormid B-564pendimethalin + pinoxaden dichlormid B-565 pendimethalin + pyroxsulamdichlormid B-566 pendimethalin + tembotrione dichlormid B-567pendimethalin + topramezone dichlormid B-568 pyroxasulfone + tembotrionedichlormid B-569 pyroxasulfone + topramezone dichlormid B-570sulfentrazone + glyphosate dichlormid B-571 terbuthylazine + H-1dichlormid B-572 terbuthylazine + foramsulfuron dichlormid B-573terbuthylazine + glyphosate dichlormid B-574 terbuthylazine + mesotrionedichlormid B-575 terbuthylazine + nicosulfuron dichlormid B-576terbuthylazine + tembotrione dichlormid B-577 terbuthylazine +topramezone dichlormid B-578 trifluralin + glyphosate dichlormid B-579clodinafop-propargyl fenchlorazole B-580 cycloxydim fenchlorazole B-581cyhalofop-butyl fenchlorazole B-582 fenoxaprop-P-ethyl fenchlorazoleB-583 pinoxaden fenchlorazole B-584 profoxydim fenchlorazole B-585tepraloxydim fenchlorazole B-586 tralkoxydim fenchlorazole B-587esprocarb fenchlorazole B-588 prosulfocarb fenchlorazole B-589thiobencarb fenchlorazole B-590 triallate fenchlorazole B-591bensulfuron-methyl fenchlorazole B-592 bispyribac-sodium fenchlorazoleB-593 cyclosulfamuron fenchlorazole B-594 flumetsulam fenchlorazoleB-595 flupyrsulfuron-methyl-sodium fenchlorazole B-596 foramsulfuronfenchlorazole B-597 imazamox fenchlorazole B-598 imazapic fenchlorazoleB-599 imazapyr fenchlorazole B-600 imazaquin fenchlorazole B-601imazethapyr fenchlorazole B-602 imazosulfuron fenchlorazole B-603iodosulfuron-methyl-sodium fenchlorazole B-604 mesosulfuronfenchlorazole B-605 nicosulfuron fenchlorazole B-606 penoxsulamfenchlorazole B-607 propoxycarbazone-sodium fenchlorazole B-608pyrazosulfuron-ethyl fenchlorazole B-609 pyroxsulam fenchlorazole B-610rimsulfuron fenchlorazole B-611 sulfosulfuron fenchlorazole B-612thiencarbazone-methyl fenchlorazole B-613 tritosulfuron fenchlorazoleB-614 2,4-D and its salts and esters fenchlorazole B-615 aminopyralidand its salts and esters fenchlorazole B-616 clopyralid and its saltsand esters fenchlorazole B-617 dicamba and its salts and estersfenchlorazole B-618 fluroxypyr-meptyl fenchlorazole B-619 quincloracfenchlorazole B-620 quinmerac fenchlorazole B-621 H-9 fenchlorazoleB-622 diflufenzopyr fenchlorazole B-623 diflufenzopyr-sodiumfenchlorazole B-624 clomazone fenchlorazole B-625 diflufenicanfenchlorazole B-626 fluorochloridone fenchlorazole B-627 isoxaflutolfenchlorazole B-628 mesotrione fenchlorazole B-629 picolinafenfenchlorazole B-630 sulcotrione fenchlorazole B-631 tefuryltrionefenchlorazole B-632 tembotrione fenchlorazole B-633 topramezonefenchlorazole B-634 H-7 fenchlorazole B-635 atrazine fenchlorazole B-636diuron fenchlorazole B-637 fluometuron fenchlorazole B-638 hexazinonefenchlorazole B-639 isoproturon fenchlorazole B-640 metribuzinfenchlorazole B-641 propanil fenchlorazole B-642 terbuthylazinefenchlorazole B-643 paraquat dichloride fenchlorazole B-644 flumioxazinfenchlorazole B-645 oxyfluorfen fenchlorazole B-646 saflufenacilfenchlorazole B-647 sulfentrazone fenchlorazole B-648 H-1 fenchlorazoleB-649 H-2 fenchlorazole B-650 glyphosate fenchlorazole B-651glyphosate-isopropylammonium fenchlorazole B-652 glyphosate-trimesium(sulfosate) fenchlorazole B-653 glufosinate fenchlorazole B-654glufosinate-ammonium fenchlorazole B-655 pendimethalin fenchlorazoleB-656 trifluralin fenchlorazole B-657 acetochlor fenchlorazole B-658cafenstrole fenchlorazole B-659 dimethenamid-P fenchlorazole B-660fentrazamide fenchlorazole B-661 flufenacet fenchlorazole B-662mefenacet fenchlorazole B-663 metazachlor fenchlorazole B-664metolachlor-S fenchlorazole B-665 pyroxasulfone fenchlorazole B-666isoxaben fenchlorazole B-667 dymron fenchlorazole B-668 indanofanfenchlorazole B-669 oxaziclomefone fenchlorazole B-670 triaziflamfenchlorazole B-671 atrazine + H-1 fenchlorazole B-672 atrazine +glyphosate fenchlorazole B-673 atrazine + mesotrione fenchlorazole B-674atrazine + nicosulfuron fenchlorazole B-675 atrazine + tembotrionefenchlorazole B-676 atrazine + topramezone fenchlorazole B-677clomazone + glyphosate fenchlorazole B-678 diflufenican +clodinafop-propargyl fenchlorazole B-679 diflufenican +fenoxaprop-P-ethyl fenchlorazole B-680 diflufenican +flupyrsulfuron-methyl-sodium fenchlorazole B-681 diflufenican +glyphosate fenchlorazole B-682 diflufenican + mesosulfuron-methylfenchlorazole B-683 diflufenican + pinoxaden fenchlorazole B-684diflufenican + pyroxsulam fenchlorazole B-685 flumetsulam + glyphosatefenchlorazole B-686 flumioxazin + glyphosate fenchlorazole B-687imazapic + glyphosate fenchlorazole B-688 imazethapyr + glyphosatefenchlorazole B-689 isoxaflutol + H-1 fenchlorazole B-690 isoxaflutol +glyphosate fenchlorazole B-691 metazachlor + H-1 fenchlorazole B-692metazachlor + glyphosate fenchlorazole B-693 metazachlor + mesotrionefenchlorazole B-694 metazachlor + nicosulfuron fenchlorazole B-695metazachlor + terbuthylazine fenchlorazole B-696 metazachlor +topramezone fenchlorazole B-697 metribuzin + glyphosate fenchlorazoleB-698 pendimethalin + H-1 fenchlorazole B-699 pendimethalin +clodinafop-propargyl fenchlorazole B-700 pendimethalin +fenoxaprop-P-ethyl fenchlorazole B-701 pendimethalin +flupyrsulfuron-methyl-sodium fenchlorazole B-702 pendimethalin +glyphosate fenchlorazole B-703 pendimethalin + mesosulfuron-methylfenchlorazole B-704 pendimethalin + mesotrione fenchlorazole B-705pendimethalin + nicosulfuron fenchlorazole B-706 pendimethalin +pinoxaden fenchlorazole B-707 pendimethalin + pyroxsulam fenchlorazoleB-708 pendimethalin + tembotrione fenchlorazole B-709 pendimethalin +topramezone fenchlorazole B-710 pyroxasulfone + tembotrionefenchlorazole B-711 pyroxasulfone + topramezone fenchlorazole B-712sulfentrazone + glyphosate fenchlorazole B-713 terbuthylazine + H-1fenchlorazole B-714 terbuthylazine + foramsulfuron fenchlorazole B-715terbuthylazine + glyphosate fenchlorazole B-716 terbuthylazine +mesotrione fenchlorazole B-717 terbuthylazine + nicosulfuronfenchlorazole B-718 terbuthylazine + tembotrione fenchlorazole B-719terbuthylazine + topramezone fenchlorazole B-720 trifluralin +glyphosate fenchlorazole B-721 clodinafop-propargyl isoxadifen B-722cycloxydim isoxadifen B-723 cyhalofop-butyl isoxadifen B-724fenoxaprop-P-ethyl isoxadifen B-725 pinoxaden isoxadifen B-726profoxydim isoxadifen B-727 tepraloxydim isoxadifen B-728 tralkoxydimisoxadifen B-729 esprocarb isoxadifen B-730 prosulfocarb isoxadifenB-731 thiobencarb isoxadifen B-732 triallate isoxadifen B-733bensulfuron-methyl isoxadifen B-734 bispyribac-sodium isoxadifen B-735cyclosulfamuron isoxadifen B-736 flumetsulam isoxadifen B-737flupyrsulfuron-methyl-sodium isoxadifen B-738 foramsulfuron isoxadifenB-739 imazamox isoxadifen B-740 imazapic isoxadifen B-741 imazapyrisoxadifen B-742 imazaquin isoxadifen B-743 imazethapyr isoxadifen B-744imazosulfuron isoxadifen B-745 iodosulfuron-methyl-sodium isoxadifenB-746 mesosulfuron isoxadifen B-747 nicosulfuron isoxadifen B-748penoxsulam isoxadifen B-749 propoxycarbazone-sodium isoxadifen B-750pyrazosulfuron-ethyl isoxadifen B-751 pyroxsulam isoxadifen B-752rimsulfuron isoxadifen B-753 sulfosulfuron isoxadifen B-754thiencarbazone-methyl isoxadifen B-755 tritosulfuron isoxadifen B-7562,4-D and its salts and esters isoxadifen B-757 aminopyralid and itssalts and esters isoxadifen B-758 clopyralid and its salts and estersisoxadifen B-759 dicamba and its salts and esters isoxadifen B-760fluroxypyr-meptyl isoxadifen B-761 quinclorac isoxadifen B-762 quinmeracisoxadifen B-763 H-9 isoxadifen B-764 diflufenzopyr isoxadifen B-765diflufenzopyr-sodium isoxadifen B-766 clomazone isoxadifen B-767diflufenican isoxadifen B-768 fluorochloridone isoxadifen B-769isoxaflutol isoxadifen B-770 mesotrione isoxadifen B-771 picolinafenisoxadifen B-772 sulcotrione isoxadifen B-773 tefuryltrione isoxadifenB-774 tembotrione isoxadifen B-775 topramezone isoxadifen B-776 H-7isoxadifen B-777 atrazine isoxadifen B-778 diuron isoxadifen B-779fluometuron isoxadifen B-780 hexazinone isoxadifen B-781 isoproturonisoxadifen B-782 metribuzin isoxadifen B-783 propanil isoxadifen B-784terbuthylazine isoxadifen B-785 paraquat dichloride isoxadifen B-786flumioxazin isoxadifen B-787 oxyfluorfen isoxadifen B-788 saflufenacilisoxadifen B-789 sulfentrazone isoxadifen B-790 H-1 isoxadifen B-791 H-2isoxadifen B-792 glyphosate isoxadifen B-793glyphosate-isopropylammonium isoxadifen B-794 glyphosate-trimesium(sulfosate) isoxadifen B-795 glufosinate isoxadifen B-796glufosinate-ammonium isoxadifen B-797 pendimethalin isoxadifen B-798trifluralin isoxadifen B-799 acetochlor isoxadifen B-800 cafenstroleisoxadifen B-801 dimethenamid-P isoxadifen B-802 fentrazamide isoxadifenB-803 flufenacet isoxadifen B-804 mefenacet isoxadifen B-805 metazachlorisoxadifen B-806 metolachlor-S isoxadifen B-807 pyroxasulfone isoxadifenB-808 isoxaben isoxadifen B-809 dymron isoxadifen B-810 indanofanisoxadifen B-811 oxaziclomefone isoxadifen B-812 triaziflam isoxadifenB-813 atrazine + H-1 isoxadifen B-814 atrazine + glyphosate isoxadifenB-815 atrazine + mesotrione isoxadifen B-816 atrazine + nicosulfuronisoxadifen B-817 atrazine + tembotrione isoxadifen B-818 atrazine +topramezone isoxadifen B-819 clomazone + glyphosate isoxadifen B-820diflufenican + clodinafop-propargyl isoxadifen B-821 diflufenican +fenoxaprop-P-ethyl isoxadifen B-822 diflufenican +flupyrsulfuron-methyl-sodium isoxadifen B-823 diflufenican + glyphosateisoxadifen B-824 diflufenican + mesosulfuron-methyl isoxadifen B-825diflufenican + pinoxaden isoxadifen B-826 diflufenican + pyroxsulamisoxadifen B-827 flumetsulam + glyphosate isoxadifen B-828 flumioxazin +glyphosate isoxadifen B-829 imazapic + glyphosate isoxadifen B-830imazethapyr + glyphosate isoxadifen B-831 isoxaflutol + H-1 isoxadifenB-832 isoxaflutol + glyphosate isoxadifen B-833 metazachlor + H-1isoxadifen B-834 metazachlor + glyphosate isoxadifen B-835 metazachlor +mesotrione isoxadifen B-836 metazachlor + nicosulfuron isoxadifen B-837metazachlor + terbuthylazine isoxadifen B-838 metazachlor + topramezoneisoxadifen B-839 metribuzin + glyphosate isoxadifen B-840pendimethalin + H-1 isoxadifen B-841 pendimethalin +clodinafop-propargyl isoxadifen B-842 pendimethalin + fenoxaprop-P-ethylisoxadifen B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifenB-844 pendimethalin + glyphosate isoxadifen B-845 pendimethalin +mesosulfuron-methyl isoxadifen B-846 pendimethalin + mesotrioneisoxadifen B-847 pendimethalin + nicosulfuron isoxadifen B-848pendimethalin + pinoxaden isoxadifen B-849 pendimethalin + pyroxsulamisoxadifen B-850 pendimethalin + tembotrione isoxadifen B-851pendimethalin + topramezone isoxadifen B-852 pyroxasulfone + tembotrioneisoxadifen B-853 pyroxasulfone + topramezone isoxadifen B-854sulfentrazone + glyphosate isoxadifen B-855 terbuthylazine + H-1isoxadifen B-856 terbuthylazine + foramsulfuron isoxadifen B-857terbuthylazine + glyphosate isoxadifen B-858 terbuthylazine + mesotrioneisoxadifen B-859 terbuthylazine + nicosulfuron isoxadifen B-860terbuthylazine + tembotrione isoxadifen B-861 terbuthylazine +topramezone isoxadifen B-862 trifluralin + glyphosate isoxadifen B-863clodinafop-propargyl mefenpyr B-864 cycloxydim mefenpyr B-865cyhalofop-butyl mefenpyr B-866 fenoxaprop-P-ethyl mefenpyr B-867pinoxaden mefenpyr B-868 profoxydim mefenpyr B-869 tepraloxydim mefenpyrB-870 tralkoxydim mefenpyr B-871 esprocarb mefenpyr B-872 prosulfocarbmefenpyr B-873 thiobencarb mefenpyr B-874 triallate mefenpyr B-875bensulfuron-methyl mefenpyr B-876 bispyribac-sodium mefenpyr B-877cyclosulfamuron mefenpyr B-878 flumetsulam mefenpyr B-879flupyrsulfuron-methyl-sodium mefenpyr B-880 foramsulfuron mefenpyr B-881imazamox mefenpyr B-882 imazapic mefenpyr B-883 imazapyr mefenpyr B-884imazaquin mefenpyr B-885 imazethapyr mefenpyr B-886 imazosulfuronmefenpyr B-887 iodosulfuron-methyl-sodium mefenpyr B-888 mesosulfuronmefenpyr B-889 nicosulfuron mefenpyr B-890 penoxsulam mefenpyr B-891propoxycarbazone-sodium mefenpyr B-892 pyrazosulfuron-ethyl mefenpyrB-893 pyroxsulam mefenpyr B-894 rimsulfuron mefenpyr B-895 sulfosulfuronmefenpyr B-896 thiencarbazone-methyl mefenpyr B-897 tritosulfuronmefenpyr B-898 2,4-D and its salts and esters mefenpyr B-899aminopyralid and its salts and esters mefenpyr B-900 clopyralid and itssalts and esters mefenpyr B-901 dicamba and its salts and estersmefenpyr B-902 fluroxypyr-meptyl mefenpyr B-903 quinclorac mefenpyrB-904 quinmerac mefenpyr B-905 H-9 mefenpyr B-906 diflufenzopyr mefenpyrB-907 diflufenzopyr-sodium mefenpyr B-908 clomazone mefenpyr B-909diflufenican mefenpyr B-910 fluorochloridone mefenpyr B-911 isoxaflutolmefenpyr B-912 mesotrione mefenpyr B-913 picolinafen mefenpyr B-914sulcotrione mefenpyr B-915 tefuryltrione mefenpyr B-916 tembotrionemefenpyr B-917 topramezone mefenpyr B-918 H-7 mefenpyr B-919 atrazinemefenpyr B-920 diuron mefenpyr B-921 fluometuron mefenpyr B-922hexazinone mefenpyr B-923 isoproturon mefenpyr B-924 metribuzin mefenpyrB-925 propanil mefenpyr B-926 terbuthylazine mefenpyr B-927 paraquatdichloride mefenpyr B-928 flumioxazin mefenpyr B-929 oxyfluorfenmefenpyr B-930 saflufenacil mefenpyr B-931 sulfentrazone mefenpyr B-932H-1 mefenpyr B-933 H-2 mefenpyr B-934 glyphosate mefenpyr B-935glyphosate-isopropylammonium mefenpyr B-936 glyphosate-trimesium(sulfosate) mefenpyr B-937 glufosinate mefenpyr B-938glufosinate-ammonium mefenpyr B-939 pendimethalin mefenpyr B-940trifluralin mefenpyr B-941 acetochlor mefenpyr B-942 cafenstrolemefenpyr B-943 dimethenamid-P mefenpyr B-944 fentrazamide mefenpyr B-945flufenacet mefenpyr B-946 mefenacet mefenpyr B-947 metazachlor mefenpyrB-948 metolachlor-S mefenpyr B-949 pyroxasulfone mefenpyr B-950 isoxabenmefenpyr B-951 dymron mefenpyr B-952 indanofan mefenpyr B-953oxaziclomefone mefenpyr B-954 triaziflam mefenpyr B-955 atrazine + H-1mefenpyr B-956 atrazine + glyphosate mefenpyr B-957 atrazine +mesotrione mefenpyr B-958 atrazine + nicosulfuron mefenpyr B-959atrazine + tembotrione mefenpyr B-960 atrazine + topramezone mefenpyrB-961 clomazone + glyphosate mefenpyr B-962 diflufenican +clodinafop-propargyl mefenpyr B-963 diflufenican + fenoxaprop-P-ethylmefenpyr B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyrB-965 diflufenican + glyphosate mefenpyr B-966 diflufenican +mesosulfuron-methyl mefenpyr B-967 diflufenican + pinoxaden mefenpyrB-968 diflufenican + pyroxsulam mefenpyr B-969 flumetsulam + glyphosatemefenpyr B-970 flumioxazin + glyphosate mefenpyr B-971 imazapic +glyphosate mefenpyr B-972 imazethapyr + glyphosate mefenpyr B-973isoxaflutol + H-1 mefenpyr B-974 isoxaflutol + glyphosate mefenpyr B-975metazachlor + H-1 mefenpyr B-976 metazachlor + glyphosate mefenpyr B-977metazachlor + mesotrione mefenpyr B-978 metazachlor + nicosulfuronmefenpyr B-979 metazachlor + terbuthylazine mefenpyr B-980 metazachlor +topramezone mefenpyr B-981 metribuzin + glyphosate mefenpyr B-982pendimethalin + H-1 mefenpyr B-983 pendimethalin + clodinafop-propargylmefenpyr B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr B-985pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr B-986pendimethalin + glyphosate mefenpyr B-987 pendimethalin +mesosulfuron-methyl mefenpyr B-988 pendimethalin + mesotrione mefenpyrB-989 pendimethalin + nicosulfuron mefenpyr B-990 pendimethalin +pinoxaden mefenpyr B-991 pendimethalin + pyroxsulam mefenpyr B-992pendimethalin + tembotrione mefenpyr B-993 pendimethalin + topramezonemefenpyr B-994 pyroxasulfone + tembotrione mefenpyr B-995pyroxasulfone + topramezone mefenpyr B-996 sulfentrazone + glyphosatemefenpyr B-997 terbuthylazine + H-1 mefenpyr B-998 terbuthylazine +foramsulfuron mefenpyr B-999 terbuthylazine + glyphosate mefenpyr B-1000terbuthylazine + mesotrione mefenpyr B-1001 terbuthylazine +nicosulfuron mefenpyr B-1002 terbuthylazine + tembotrione mefenpyrB-1003 terbuthylazine + topramezone mefenpyr B-1004 trifluralin +glyphosate mefenpyr B-1005 clodinafop-propargyl H-12 B-1006 cycloxydimH-12 B-1007 cyhalofop-butyl H-12 B-1008 fenoxaprop-P-ethyl H-12 B-1009pinoxaden H-12 B-1010 profoxydim H-12 B-1011 tepraloxydim H-12 B-1012tralkoxydim H-12 B-1013 esprocarb H-12 B-1014 prosulfocarb H-12 B-1015thiobencarb H-12 B-1016 triallate H-12 B-1017 bensulfuron-methyl H-12B-1018 bispyribac-sodium H-12 B-1019 cyclosulfamuron H-12 B-1020flumetsulam H-12 B-1021 flupyrsulfuron-methyl-sodium H-12 B-1022foramsulfuron H-12 B-1023 imazamox H-12 B-1024 imazapic H-12 B-1025imazapyr H-12 B-1026 imazaquin H-12 B-1027 imazethapyr H-12 B-1028imazosulfuron H-12 B-1029 iodosulfuron-methyl-sodium H-12 B-1030mesosulfuron H-12 B-1031 nicosulfuron H-12 B-1032 penoxsulam H-12 B-1033propoxycarbazone-sodium H-12 B-1034 pyrazosulfuron-ethyl H-12 B-1035pyroxsulam H-12 B-1036 rimsulfuron H-12 B-1037 sulfosulfuron H-12 B-1038thiencarbazone-methyl H-12 B-1039 tritosulfuron H-12 B-1040 2,4-D andits salts and esters H-12 B-1041 aminopyralid and its salts and estersH-12 B-1042 clopyralid and its salts and esters H-12 B-1043 dicamba andits salts and esters H-12 B-1044 fluroxypyr-meptyl H-12 B-1045quinclorac H-12 B-1046 quinmerac H-12 B-1047 H-9 H-12 B-1048diflufenzopyr H-12 B-1049 diflufenzopyr-sodium H-12 B-1050 clomazoneH-12 B-1051 diflufenican H-12 B-1052 fluorochloridone H-12 B-1053isoxaflutol H-12 B-1054 mesotrione H-12 B-1055 picolinafen H-12 B-1056sulcotrione H-12 B-1057 tefuryltrione H-12 B-1058 tembotrione H-12B-1059 topramezone H-12 B-1060 H-7 H-12 B-1061 atrazine H-12 B-1062diuron H-12 B-1063 fluometuron H-12 B-1064 hexazinone H-12 B-1065isoproturon H-12 B-1066 metribuzin H-12 B-1067 propanil H-12 B-1068terbuthylazine H-12 B-1069 paraquat dichloride H-12 B-1070 flumioxazinH-12 B-1071 oxyfluorfen H-12 B-1072 saflufenacil H-12 B-1073sulfentrazone H-12 B-1074 H-1 H-12 B-1075 H-2 H-12 B-1076 glyphosateH-12 B-1077 glyphosate-isopropylammonium H-12 B-1078glyphosate-trimesium (sulfosate) H-12 B-1079 glufosinate H-12 B-1080glufosinate-ammonium H-12 B-1081 pendimethalin H-12 B-1082 trifluralinH-12 B-1083 acetochlor H-12 B-1084 cafenstrole H-12 B-1085dimethenamid-P H-12 B-1086 fentrazamide H-12 B-1087 flufenacet H-12B-1088 mefenacet H-12 B-1089 metazachlor H-12 B-1090 metolachlor-S H-12B-1091 pyroxasulfone H-12 B-1092 isoxaben H-12 B-1093 dymron H-12 B-1094indanofan H-12 B-1095 oxaziclomefone H-12 B-1096 triaziflam H-12 B-1097atrazine + H-1 H-12 B-1098 atrazine + glyphosate H-12 B-1099 atrazine +mesotrione H-12 B-1100 atrazine + nicosulfuron H-12 B-1101 atrazine +tembotrione H-12 B-1102 atrazine + topramezone H-12 B-1103 clomazone +glyphosate H-12 B-1104 diflufenican + clodinafop-propargyl H-12 B-1105diflufenican + fenoxaprop-P-ethyl H-12 B-1106 diflufenican +flupyrsulfuron-methyl-sodium H-12 B-1107 diflufenican + glyphosate H-12B-1108 diflufenican + mesosulfuron-methyl H-12 B-1109 diflufenican +pinoxaden H-12 B-1110 diflufenican + pyroxsulam H-12 B-1111flumetsulam + glyphosate H-12 B-1112 flumioxazin + glyphosate H-12B-1113 imazapic + glyphosate H-12 B-1114 imazethapyr + glyphosate H-12B-1115 isoxaflutol + H-1 H-12 B-1116 isoxaflutol + glyphosate H-12B-1117 metazachlor + H-1 H-12 B-1118 metazachlor + glyphosate H-12B-1119 metazachlor + mesotrione H-12 B-1120 metazachlor + nicosulfuronH-12 B-1121 metazachlor + terbuthylazine H-12 B-1122 metazachlor +topramezone H-12 B-1123 metribuzin + glyphosate H-12 B-1124pendimethalin + H-1 H-12 B-1125 pendimethalin + clodinafop-propargylH-12 B-1126 pendimethalin + fenoxaprop-P-ethyl H-12 B-1127pendimethalin + flupyrsulfuron-methyl-sodium H-12 B-1128 pendimethalin +glyphosate H-12 B-1129 pendimethalin + mesosulfuron-methyl H-12 B-1130pendimethalin + mesotrione H-12 B-1131 pendimethalin + nicosulfuron H-12B-1132 pendimethalin + pinoxaden H-12 B-1133 pendimethalin + pyroxsulamH-12 B-1134 pendimethalin + tembotrione H-12 B-1135 pendimethalin +topramezone H-12 B-1136 pyroxasulfone + tembotrione H-12 B-1137pyroxasulfone + topramezone H-12 B-1138 sulfentrazone + glyphosate H-12B-1139 terbuthylazine + H-1 H-12 B-1140 terbuthylazine + foramsulfuronH-12 B-1141 terbuthylazine + glyphosate H-12 B-1142 terbuthylazine +mesotrione H-12 B-1143 terbuthylazine + nicosulfuron H-12 B-1144terbuthylazine + tembotrione H-12 B-1145 terbuthylazine + topramezoneH-12 B-1146 trifluralin + glyphosate H-12 B-1147 2-1 — B-1148 2-2 —B-1149 2-3 — B-1150 2-4 — B-1151 2-5 — B-1152 2-6 — B-1153 2-7 — B-11542-8 — B-1155 2-9 — B-1156 2-1 benoxacor B-1157 2-2 benoxacor B-1158 2-3benoxacor B-1159 2-4 benoxacor B-1160 2-5 benoxacor B-1161 2-6 benoxacorB-1162 2-7 benoxacor B-1163 2-8 benoxacor B-1164 2-9 benoxacor B-11652-1 cloquintocet B-1166 2-2 cloquintocet B-1167 2-3 cloquintocet B-11682-4 cloquintocet B-1169 2-5 cloquintocet B-1170 2-6 cloquintocet B-11712-7 cloquintocet B-1172 2-8 cloquintocet B-1173 2-9 cloquintocet B-11742-1 cyprosulfamide B-1175 2-2 cyprosulfamide B-1176 2-3 cyprosulfamideB-1177 2-4 cyprosulfamide B-1178 2-5 cyprosulfamide B-1179 2-6cyprosulfamide B-1180 2-7 cyprosulfamide B-1181 2-8 cyprosulfamideB-1182 2-9 cyprosulfamide B-1183 2-1 dichlormid B-1184 2-2 dichlormidB-1185 2-3 dichlormid B-1186 2-4 dichlormid B-1187 2-5 dichlormid B-11882-6 dichlormid B-1189 2-7 dichlormid B-1190 2-8 dichlormid B-1191 2-9dichlormid B-1192 2-1 fenchlorazole B-1193 2-2 fenchlorazole B-1194 2-3fenchlorazole B-1195 2-4 fenchlorazole B-1196 2-5 fenchlorazole B-11972-6 fenchlorazole B-1198 2-7 fenchlorazole B-1199 2-8 fenchlorazoleB-1200 2-9 fenchlorazole B-1201 2-1 isoxadifen B-1202 2-2 isoxadifenB-1203 2-3 isoxadifen B-1204 2-4 isoxadifen B-1205 2-5 isoxadifen B-12062-6 isoxadifen B-1207 2-7 isoxadifen B-1208 2-8 isoxadifen B-1209 2-9isoxadifen B-1210 2-1 mefenpyr B-1211 2-2 mefenpyr B-1212 2-3 mefenpyrB-1213 2-4 mefenpyr B-1214 2-5 mefenpyr B-1215 2-6 mefenpyr B-1216 2-7mefenpyr B-1217 2-8 mefenpyr B-1218 2-9 mefenpyr B-1219 2-1 H-11 B-12202-2 H-11 B-1221 2-3 H-11 B-1222 2-4 H-11 B-1223 2-5 H-11 B-1224 2-6 H-11B-1225 2-7 H-11 B-1226 2-8 H-11 B-1227 2-9 H-11 B-1228 2-1 H-12 B-12292-2 H-12 B-1230 2-3 H-12 B-1231 2-4 H-12 B-1232 2-5 H-12 B-1233 2-6 H-12B-1234 2-7 H-12 B-1235 2-8 H-12 B-1236 2-9 H-12

The compounds I and the compositions according to the invention may alsohave a plant-strengthening action. Accordingly, they are suitable formobilizing the defense system of the plants against attack by unwantedmicroorganisms, such as harmful fungi, but also viruses and bacteria.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defense system of treated plants in sucha way that, when subsequently inoculated by unwanted microorganisms, thetreated plants display a substantial degree of resistance to thesemicroorganisms.

The compounds I can be employed for protecting plants against attack byunwanted microorganisms within a certain period of time after thetreatment. The period of time within which their protection is effectedgenerally extends from 1 to 28 days, preferably from 1 to 14 days, afterthe treatment of the plants with the compounds I, or, after treatment ofthe seed, for up to 9 months after sowing.

The compounds I and the compositions according to the invention are alsosuitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by theplants.

The following examples will further illustrate the invention:

With appropriate modification of the starting materials, the proceduresgiven in the synthesis examples below were used to obtain furthercompounds I. The compounds obtained in this manner are listed in thetable that follows, together with physical data. The products shownbelow were characterized by determination of the melting point, NMRspectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography coupled with massspectrometry:

HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA,Germany), 50*4.6 mm; mobile phase: acetonitrile+0.1% trifluoroaceticacid (TFA)/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5minutes at 40° C., flow rate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive mode).

DMF: N,N-Dimethyl formamide

DBU: 1,8-Diazabicyclo[5 5.4.0]undec-7-ene

EtOAc: acetic acid ethyl ester

LiHMDS: Lithium bis(trimethylsilyl)amide

EXAMPLE 1 Preparation of4-chloro-N-(4-methyl-1,2,5-oxadiazol-3-yl)-1,1-dioxo-2,3-dihydrobenzothiophene-5-carboxamide(Corresponds to compound A-1, Table 1)

Step 1)

To a solution of carboxylic acid 1 (3 g, 12.2 mmol), prepared accordingto WO 2000020408, in CH₂Cl₂ (50 mL) were added 2 drops of DMF and oxalylchloride (1.5 mL, 13.4 mmol) at ambient temperature. The reactionmixture was allowed to stir for 18 hours, then concentrated underreduced pressure. The crude product (2) was used without furtherpurification in the subsequent step.

Step 2)

To a solution of 4-methyl-1,2,5-oxadiazol-3-amine 3 (200 mg, 2.0 mmol)in THF (70 mL) was added LiHMDS (1.0 M solution in THF, 2.2 m L, 2.2mmol) at −78° C. under a nitrogen atmosphere. The mixture was allowed tostir at −78° C. for 1 hour followed by the addition of a solution ofacid chloride 2 (535 mg, 2.0 mmol) in THF (10 mL). The reaction wasallowed to warm to ambient temperature and stirred for 18 hours. Thereaction mixture was quenched by slow addition of saturated aqueousNH₄Cl (40 mL) and the aqueous layer was extracted with EtOAc (3×50 mL).The combined organic layers were washed with saturated brine (30 mL),dried (MgSO₄) and concentrated. Purification of the obtained residue bypreparative HPLC afforded the desired product A-1 of table 1 (120 mg,18%). ¹H NMR (CDCl₃ 400 MHz): δ 7.97-7.85 (m, 2H), 7.79 (d, 1H), 4.19(s, 3H), 3.63-3.58 (m, 2H), 3.48-3.42 (m, 2H).

Preparative HPLC Purification:

-   Column: Nucleodur C18 Gravity 5 μm (Macherey-Nagel GmbH & Co. KG,    Germany); Column diameter: 50*100 mm;-   Mobile phase: acetonitrile+0.05% trifluoroacetic acid    (TFA)/water+0.05% TFA, using a gradient from 25:75 to 70:30 over 7.5    minutes at 25° C., flow rate 128 ml/min.

By analogy to the methods described in Example 1 the following compoundsof formula I′ of table 4 and of formula I″ of table 5 were prepared:

TABLE 4 (I′)

MS R¹ CYC R³ (m/z) I′.A-1 Cl Cyc-1a′-1 — 328.2 I′.A-8 Cl Cyc-1c′ — 370.2I′.A-35 CH₃ Cyc-1c′ — 350.2 I′.A-47 CH₃ Cyc-1f′-1 — 365.1 I′.A-49 CH₃Cyc-1g′ — 336.1 I′.A-113 — Cyc-2a′ Cl 289.2 I′.A-117 — Cyc-2a′ Br 335.0I′.A-129 — Cyc-2a′ OCH₃ 285.3 Cyc-1a′-1

Cyc-1c′

Cyc-1f′-1

Cyc-1g′

Cyc-2a′

TABLE 5 (I″)

MS R¹ CYC R³ (m/z) I″.A-1 Cl Cyc-1a′-1 — 344.2 I″.A-8 Cl Cyc-1c′ — 386.2

II. Use Examples

The herbicidal activity of the compounds of the formula I wasdemonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this has been impaired bythe active ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. For this purpose, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A goodherbicidal activity is given at values of at least 70 and a very goodherbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments belonged to the followingspecies:

Bayer Code Scientific name English name ABUTH Abutilon theophrastivelvetleaf AMARE Amaranthus retroflexus common amaranth ALOMY Alopecurusmyosuroides blackgrass APESV Apera spica-venti bentgrass, silky AVEFAAvena fatua wild oat CHEAL Chenopodium album lampsquaters ECHCGEchinochloa crus-galli comon barnyardgrass POLCO Polygonum convulvulusbindweed, black SETVI Setaria viridis green foxtail

At an application rate of 1 kg/ha, the compounds I′.A-35, I.′A-47 andI′.A-49, applied by the post-emergence method, showed very goodherbicidal activity against ABUTH.

At an application rate of 1 kg/ha, the compounds I′.A-113, applied bythe post-emergence method, showed good herbicidal activity againstABUTH.

At an application rate of 1 kg/ha, the compound I′.A-35, I.′A-47 andI′.A-49, applied by the pre-emergence method, showed very goodherbicidal activity against ABUTH.

At an application rate of 0.25 kg/ha, the compounds I.′A-1, I″.A-1,I′.A-8 and I″.A-8 applied by the post-emergence method, showed very goodherbicidal activity against AMARE.

At an application rate of 0.25 kg/ha, the compounds I.′A-1, I″.A-1,I′.A-8 and I″.A-8 applied by the pre-emergence method, showed very goodherbicidal activity against AMARE.

At an application rate of 0.25 kg/ha, the compounds I″.A-1 and I″.A-8applied by the post-emergence method, showed very good herbicidalactivity against AVEFA.

At an application rate of 0.25 kg/ha, the compound I″.A-8 applied by thepost-emergence method, showed very good herbicidal activity againstALOMY.

At an application rate of 0.25 kg/ha, the compounds I.′A-1, I″.A-1,I′.A-8 and I″.A-8 applied by the post-emergence method, showed very goodherbicidal activity against CHEAL.

At an application rate of 0.25 kg/ha, the compounds I.′A-1, I″.A-1,I′.A-8 and I″.A-8 applied by the post-emergence method, showed very goodherbicidal activity against POLCO.

At an application rate of 0.25 kg/ha, the compounds I″.A-1, I′.A-8 andI″.A-8 applied by the post-emergence method, showed very good herbicidalactivity against SETVI.

At an application rate of 0.25 kg/ha, the compounds I″.A-1, I′.A-8 andI″.A-8 applied by the post-emergence method, showed very good herbicidalactivity against ECHCG.

At an application rate of 0.25 kg/ha, the compounds I″.A-1 and I″.A-8applied by the pre-emergence method, showed very good herbicidalactivity against ECHCG.

At an application rate of 0.25 kg/ha, the compounds I″.A-1 and I″.A-8applied by the pre-emergence method, showed very good herbicidalactivity against APESV.

We claim:
 1. A compound of formula I,

wherein R is selected from the group consisting of hydrogen, cyano,nitro, halogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aformentioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, O—R^(a), Z—S(O)_(n)—R^(b), Z—C(═O)—R^(c),Z—C(═O)—OR^(d), Z—C(═O)—NR^(e)R^(f), Z—NR^(g)R^(h), Z-phenyl andZ-heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic or8-, 9- or 10-membered bicyclic saturated, partially unsaturated oraromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ringmembers, which are selected from the group consisting of O, N and S,where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2,3 or 4 groups R′, which are identical or different; CYC indicates a bi-or tricyclic radical of the following formulae Cyc-1 or Cyc-2

where # indicates the point of attachment of the bicyclic radical to thecarbonyl group, Q, Q′ independently of each other indicate a fused 5-,6-, 7-, 8-, 9- or 10-membered heterocycle, where the fused heterocyclehas 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, Sand N as ring members, where the fused heterocycle is monocyclic orbicyclic and where the fused heterocycle is unsubstituted or carries 1,2, 3, 4, 5, 6, 7, 8, 9 or 10 radicals R²; R¹ in formula Cyc-1 isselected from the group consisting of Z¹-cyano, halogen, nitro,C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl,C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, Z¹-C₁-C₄-alkoxy-C₁-C₄-alkoxy,C₁-C₄-alkylthio-C₁-C₄-alkyl, Z¹-C₁-C₄-alkylthio-C₁-C₄-alkylthio,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, Z¹-C₁-C₄-haloalkoxy-C₁-C₄-alkoxy,Z¹—S(O)_(k)—R^(1b), Z¹-phenoxy and Z¹-heterocyclyloxy, whereheterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9-or 10-membered bicyclic saturated, partially unsaturated or aromaticheterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members,which are selected from the group consisting of O, N and S, where thecyclic groups in phenoxy and heterocyclyloxy are unsubstituted orsubstituted by 1, 2, 3 or 4 groups R¹¹, which are identical ordifferent; R² is selected from the group consisting of halogen, Z²—OH,Z²—NO₂, Z²-cyano, oxo (═O), ═N—R²², C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, Z²-C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, Z²-C₁-C₄-haloalkoxy,Z²-C₃-C₁₀-cycloalkyl,O—Z²-C₃-C₁₀-cycloalkyl, Z²-(tri-C₁-C₄-alkyl)silyl,Z²—S(O)_(k)—R^(2b), Z²—C(═O)—R^(2c), Z²—NR^(2g)R^(2h) and Z²-phenyl,where phenyl in Z²-phenyl is unsubstituted or substituted by 1, 2, 3 or4 groups R²¹, which are identical or different; R³ in formula Cyc-2 isselected from the group consisting of hydrogen, halogen, Z³—OH, Z³—NO₂,Z³-cyano, C₁-C6-alkyl, C₂-C₈-alkenyl, C₂-C₈alkynyl,Z³-C₃-C₁₀-cycloalkyl, Z³-C₃-C₁₀-cycloalkoxy, where the C₃-C₁₀-cycloalkylgroups in the two aformentioned radicals are unsubstituted or partiallyor completely halogenated, C₁-C₈-haloalkyl, Z³-C₁-C₈-alkoxy,Z³-C₁-C₈-haloalkoxy, Z³-C₁-C₄-alkoxy-C₁-C₄-alkoxy,Z³-C₁-C₄-alkylthio-C₁-C₄-alkylthio, Z³-C₂-C₈-alkenyloxy,Z³-C₂-C₈-alkynyloxy, Z³-C₁-C₈-haloalkoxy,Z³-C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, Z³-(tri-C₁-C₄-alkyl)silyl,Z³—S(O)_(k)—R^(3b), Z³—C(═O)—R^(3c), Z³—C(═O)—OR^(3d),Z³—C(═O)—NR^(3e)R^(3f), Z³—NR^(3g)R^(3h), Z^(3a)-phenyl andZ^(3a)-heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclicor 8-, 9- or 10-membered bicyclic saturated, partially unsaturated oraromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ringmembers, which are selected from the group consisting of O, N and S,where the cyclic groups in Z^(3a)-phenyl and Z^(3a)-heterocyclyl areunsubstituted or substituted by 1, 2, 3 or 4 groups R³¹, which areidentical or different; R⁴ is selected from the group consisting ofhydrogen, halogen, cyano, nitro, C₁-C₄-alkyl and C₁-C₄-haloalkyl; R⁵ isselected from the group consisting of hydrogen, halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl; n is 0, 1 or 2; k is 0, 1 or 2; R′, R¹¹, R²¹, R³¹independently of each other are selected from the group consisting ofhalogen, NO₂, CN, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkoxy and C₁-C₆-haloalkyloxy;R²² is selected from the group consisting of C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and C₃-C₇-cycloalkoxy, which is unsubstituted orpartially or completely halogenated; Z, Z¹, Z², Z³ independently of eachother are selected from the group consisting of a covalent bond andC₁-C₄-alkanediyl; Z^(3a) is selected from the group consisting of acovalent bond, C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-Oand C₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl; R^(a) is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aformentioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2, 3 or 4 groups, which are identical or different and selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; R^(b), R^(1b), R^(2b), R^(3b) independently ofeach other are selected from the group consisting of C₁-C₆-alkyl,C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl and phenyl, where phenyl isunsubstituted or substituted by 1, 2, 3 or 4 groups, which are identicalor different and selected from the group consisting of halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(c),R^(2c), R^(3c) independently of each other are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aforementioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl,benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-memberedmonocyclic saturated, partially unsaturated or aromatic heterocycle,which contains 1, 2, 3 or 4 heteroatoms as ring members, which areselected from the group consisting of O, N and S, where phenyl, benzyland heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groupsselected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(d), R^(3d)independently of each other are selected from the group consisting ofC₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where theC₃-C₇-cycloalkyl groups in the two aformentioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl areunsubstituted or substituted by 1, 2, 3 or 4 groups, which are identicalor different and selected from the group consisting of halogen,C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(e),R^(f) independently of each other are selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aformentioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2, 3 or 4 groups, which are identical or different and selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy, or R^(e), R^(f) together with the nitrogen atom,to which they are bound may form a 5-, 6- or 7-membered, saturated orunsaturated N-bound heterocyclic radical, which may carry as a ringmember a further heteroatom selected from the group consisting of O, Sand N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, whichare identical or different and selected from the group consisting ofhalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; R^(3e), R^(3f) independently of each other have themeanings given for R^(e), R^(f); R^(g) is selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in thetwo aformentioned radicals are unsubstituted or partially or completelyhalogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl andbenzyl, where phenyl and benzyl are unsubstituted or substituted by 1,2, 3 or 4 groups, which are identical or different and selected from thegroup consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkoxy; R^(h) is selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,where the C₃-C₇-cycloalkyl groups in the two aformentioned radicals areunsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, a radical C(═O)—R^(k), phenyl and benzyl,where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4groups, which are identical or different and selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy, or R^(g), R^(h) together with the nitrogen atom, towhich they are bound may form a 5-, 6 or 7-membered, saturated orunsaturated N-bound heterocyclic radical, which may carry as a ringmember a further heteroatom selected from O, S and N and which isunsubstituted or may carry 1, 2, 3 or 4 groups, which are identical ordifferent and selected from the group consisting of ═O,halogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;R^(2g), R^(2h) independently of each other have the meanings given forR^(g), R^(h); R^(3g), R^(3h) independently of each other have themeanings given for R^(g), R^(h); R^(k) has the meanings given for R^(c);an N-oxide or an agriculturally suitable salt thereof.
 2. The compoundas claimed in claim 1, where R is selected from the group consisting ofhalogen, cyano, nitro, NH₂, C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C(═O)—R^(e), C(═O)—OR^(d),C(═O)—NR^(e)R^(f) and NH—C(═O)R^(k), where R^(c) is C₁-C₄-alkyl orC₁-C₄-haloalkyl, R^(d) is C₁-C₄-alkyl, R^(e) is hydrogen or C₁-C₄-alkyl,R^(f) is hydrogen or C₁-C₄-alkyl, or R^(e), R^(f) together with thenitrogen atom, to which they are bound may form a 5-, 6-, or 7-membered,saturated N-bound heterocyclic radical, which may carry as a ring membera further heteroatom selected from O, S and N and which is unsubstitutedor may carry 1, 2, 3 or 4 methyl groups, R^(k) is C₁-C₄-alkyl.
 3. Thecompound as claimed in claim 1, where R is a radical OR^(a), where R^(a)is selected from the group consisting of H, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted orpartly or completely halogenated.
 4. The compound as claimed in claim 1,where R is phenyl or heterocyclyl, where heterocyclyl is a 5- or6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated,partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or4 heteroatoms as ring members, which are selected from the groupconsisting of O, N and S, where phenyl and heterocyclyl areunsubstituted or substituted by 1, 2, 3 or 4 groups R′, where R′ isselected from the group consisting of halogen, methyl, ethyl, methoxyand trifluoromethyl.
 5. The compound as claimed in claim 1, where R isS(O)_(n—R) ^(b), where R^(b) is C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl, orphenyl.
 6. The compound as claimed in claim 1, wherein R² is selectedfrom the group consisting of oxo, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkylthio, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio,C₃-C₄-alkenyl, C₃-C₄-alkynyl, and ═N—R²², where R²² is C₁-C₄-alkoxy. 7.The compound as claimed in claim 1, wherein R² is selected from thegroup consisting of oxo, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₃-C₄-alkenyl, and ═N—R²², where R²²is C₁-C₄-alkoxy.
 8. The compound as claimed in claim 1, wherein R⁴ isselected from the group consisting of hydrogen, CN, CHF₂, CF₃, CH₃, NO₂and halogen.
 9. The compound as claimed in claim 1, wherein R⁵ isselected from the group consisting of hydrogen, halogen, CHF₂ and CF₃.10. The compound of the formula I according to claim 1, wherein R⁴ andR⁵ are hydrogen.
 11. The compound as claimed in claim 1, where CYC is aradical Cyc-1.
 12. The compound as claimed in claim 11, where Qindicates a fused 5- or 6-membered monocyclic hetorcycle or a fused 7-,8-, 9- or 10-membered spiro-bicyclic heterocycle, where the fusedmonocyclic heterocycle has 1 or 2 heteroatoms selected from O, S and Nas ring members and is unsubstituted or carries 1, 2, 3, 4, 5, 6, 7 or 8radicals R², where the fused spiro-bicyclic heterocycle has 1, 2, 3 or 4heteroatoms selected from O, S and N as ring members and isunsubstituted or carries 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 radicals R².13. The compound as claimed in claim 11, where R¹ in formula Cyc-1 isselected from the group consisting of cyano, halogen, nitro,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,Z¹—C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-alkylthio-C₁-C₄-alkyl,Z¹—C₁-C₄-alkylthio-C₁-C₄-alkylthio, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₆-haloalkoxy, and S(O)_(k)R^(1b), where R_(1b) is selected from thegroup consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl.
 14. The compound asclaimed in claim 11, where R¹ is selected from the group consisting ofhalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsufonyl.
 15. Thecompound as claimed in claim 11, where Cyc-1 is selected from thefollowing groups Cyc-1a to Cyc-1h:

where R⁵ is hydrogen or halogen, and where R²³ and R²⁴ are hydrogen orhave one of the meanings given for R².
 16. The compound as claimed inclaim 11, where Cyc-1 is selected from the following groups Cyc-1a′ toCyc-1h′ and Cyc-1 f′:

where R^(2p), R^(2q) are independently of each other hydrogen,C₁-C₄-alkyl or C₁-C₄-alkoxy; R^(2r), R^(2s) are independently of eachother hydrogen or halogen; R^(2t) is C₁-C₄-haloalkoxy; R^(2u) isC₁-C₄-alkoxy; R^(2v) is C₁-C₄-alkyl or C₃-C₄-alkenyl.
 17. The compoundas claimed in claim 1, where CYC is a radical Cyc-2.
 18. The compound asclaimed in claim 17, where Q′ indicates a fused 5- or 6-memberedmonocyclic heterocycle or a fused 7-, 8-, 9- or 10-membered bicyclicheterocycle, where the fused monocyclic heterocycle has 1 or 2heteroatoms selected from O, S and N as ring members and isunsubstituted or carries 1, 2, 3, 4, 5, 6, 7 or 8 radicals R², where thefused bicyclic heterocycle has 1, 2, 3 or 4 heteroatoms selected from O,S and N as ring members and is unsubstituted or carries 1, 2, 3, 4, 5,6, 7, 8, 9 or 10 radicals R².
 19. The compound as claimed in claim 17,where R³ is selected from the group consisting of hydrogen, cyano,halogen, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-alkenyloxy,C₂-C₄-alkynyloxy and S(O)_(k)R^(3b).
 20. The compound as claimed inclaim 17, where R³ is selected from the group consisting of hydrogen,halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,S(O)₂—C₁-C₄-alkyl and S(O)₂—C₁-C₄-haloalkyl.
 21. The compound as claimedin claim 17, where Cyc-2 is selected from the following groups Cyc-2a toCyc-2d:

where # p is 0, 1, 2 or
 3. 22. The compound as claimed in claim 17,where p is 0 and R⁴ is hydrogen.
 23. The compound as claimed in claim17, where R³ is selected from the group consisting of hydrogen, halogen,C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.
 24. A compositioncomprising at least one compound as claimed in claim 1 and at least oneauxiliary, which is customary for formulating crop protection compounds.25. A method for controlling unwanted vegetation which comprisestreating the unwanted vegetation, their seed or their habitat with aherbicidally effective amount of at least one compound as claimed inclaim 1.